JPS6143348B2 - - Google Patents
Info
- Publication number
- JPS6143348B2 JPS6143348B2 JP11847381A JP11847381A JPS6143348B2 JP S6143348 B2 JPS6143348 B2 JP S6143348B2 JP 11847381 A JP11847381 A JP 11847381A JP 11847381 A JP11847381 A JP 11847381A JP S6143348 B2 JPS6143348 B2 JP S6143348B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- methyl
- group
- pyrimidinone
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- UAUSQEVPWPGBHG-IHWYPQMZSA-N (z)-3-aminobut-2-enamide Chemical compound C\C(N)=C\C(N)=O UAUSQEVPWPGBHG-IHWYPQMZSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- -1 2-(1-acetamino-3-methylbutyl) -6-Methyl-4(3H)-pyrimidinone Chemical compound 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- QWIDYOLZFAQBOB-UHFFFAOYSA-N 2-methyl-1h-pyrimidin-6-one Chemical compound CC1=NC=CC(=O)N1 QWIDYOLZFAQBOB-UHFFFAOYSA-N 0.000 description 1
- LHRIUKSRPHFASO-UHFFFAOYSA-N 6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(=O)N=CN1 LHRIUKSRPHFASO-UHFFFAOYSA-N 0.000 description 1
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 1
- QIAFMBKCNZACKA-UHFFFAOYSA-N Hippuric acid Natural products OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- YIVZYFDBEPMPNL-LBPRGKRZSA-N ethyl (2s)-2-acetamido-3-phenylpropanoate Chemical compound CCOC(=O)[C@@H](NC(C)=O)CC1=CC=CC=C1 YIVZYFDBEPMPNL-LBPRGKRZSA-N 0.000 description 1
- CVLYKMBNKKBAHO-VIFPVBQESA-N ethyl (2s)-2-acetamido-4-methylpentanoate Chemical compound CCOC(=O)[C@H](CC(C)C)NC(C)=O CVLYKMBNKKBAHO-VIFPVBQESA-N 0.000 description 1
- BFNYDDPQMKYKKJ-YFKPBYRVSA-N ethyl (2s)-2-acetamidopropanoate Chemical compound CCOC(=O)[C@H](C)NC(C)=O BFNYDDPQMKYKKJ-YFKPBYRVSA-N 0.000 description 1
- IGDJNTXVYYFXGD-UHFFFAOYSA-N ethyl 2-(2-methylpropanoylamino)acetate Chemical compound CCOC(=O)CNC(=O)C(C)C IGDJNTXVYYFXGD-UHFFFAOYSA-N 0.000 description 1
- AMBDTBHJFINMSE-UHFFFAOYSA-N ethyl 2-acetamidoacetate Chemical compound CCOC(=O)CNC(C)=O AMBDTBHJFINMSE-UHFFFAOYSA-N 0.000 description 1
- PTXRQIPIELXJFH-UHFFFAOYSA-N ethyl 2-benzamidoacetate Chemical compound CCOC(=O)CNC(=O)C1=CC=CC=C1 PTXRQIPIELXJFH-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- RFNPAJMKCOVSRV-UHFFFAOYSA-N n-[(6-methyl-4-oxo-1h-pyrimidin-2-yl)methyl]acetamide Chemical compound CC(=O)NCC1=NC(=O)C=C(C)N1 RFNPAJMKCOVSRV-UHFFFAOYSA-N 0.000 description 1
- CJZCJBGDGNEDPL-UHFFFAOYSA-N n-[(6-methyl-4-oxo-1h-pyrimidin-2-yl)methyl]benzamide Chemical compound N1C(C)=CC(=O)N=C1CNC(=O)C1=CC=CC=C1 CJZCJBGDGNEDPL-UHFFFAOYSA-N 0.000 description 1
- YYAVCOIGYQHORE-UHFFFAOYSA-N n-[1-(6-methyl-4-oxo-1h-pyrimidin-2-yl)ethyl]acetamide Chemical compound CC(=O)NC(C)C1=NC(=O)C=C(C)N1 YYAVCOIGYQHORE-UHFFFAOYSA-N 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明は２―（１―アシルアミノアルキル）―
６―メチル―４（3H）―ピリミジノン（一般式
式中R1は水素、直鎖又は枝分れした低級アル
キル基、あるいはアラルキル基、R2は低級アル
キル基又はアリール基を意味する）の製法に関す
るものである。而してその意図するところは医薬
品あるいは農薬の中間体として価値ある上記化合
物を経済的に有利に製造するところにある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 2-(1-acylaminoalkyl)-
Process for producing 6-methyl-4(3H)-pyrimidinone (in the general formula, R 1 means hydrogen, a linear or branched lower alkyl group, or an aralkyl group, and R 2 means a lower alkyl group or an aryl group) It is related to. The intention is to economically advantageously produce the above-mentioned compounds that are valuable as intermediates for pharmaceuticals or agricultural chemicals.
本発明により得られる化合物は、いづれも新
規の化合物であるが、若し従来の方法でこのもの
を製造するとすれば先ずピリミジノンを含成し、
後に２位を修飾する方法が妥当である。例えばア
セト酢酸エステルあるいはジケテンを尿素、チオ
尿素などと反応せしめウラシル誘導体を製造し
（たとえばR.N.Racey.J.Chem.Soc.，1954，
830）、次に２位を修飾して行く方法が考えられ
る。 The compounds obtained by the present invention are all new compounds, but if they were to be produced by conventional methods, they would first contain pyrimidinone,
An appropriate method is to modify the 2nd position later. For example, uracil derivatives are produced by reacting acetoacetate or diketene with urea, thiourea, etc. (for example, RNRacey.J.Chem.Soc., 1954,
830), and then modifying the 2nd position may be considered.
これに対し本発明の特徴とするところは原料で
ある３―アミノクロトンアミド（）はジケテン
とアンモニヤとより定量的に得られ、また化合物
も市販のα―アミノ酸より容易に得られるこ
と、反応が一行程で進行、収率も良好である点に
ある。たとえば化合物と馬尿酸エチル（一般式
、式中R1は水素、R2はフエニル、R3はエチル
基を意味する）とをメタノール中ナトリウムメト
キサイドの存在加熱還流すると、２―（１―ベン
ゾイルアミノメチル）―６―メチル―４―
（3H）ピリミジノン（一般式、式中R1は水素、
R2はフエニル基を意味する）を好収率で得る。 In contrast, the characteristics of the present invention are that the raw material 3-aminocrotonamide () can be obtained quantitatively from diketene and ammonia, and that the compound can be easily obtained from commercially available α-amino acids, and that the reaction is easy. The process proceeds in one step and the yield is good. For example, when a compound and ethyl hippurate (general formula, in which R 1 means hydrogen, R 2 means phenyl, and R 3 means ethyl group) are heated under reflux in methanol in the presence of sodium methoxide, 2-(1-benzoyl aminomethyl)-6-methyl-4-
(3H) Pyrimidinone (general formula, in which R 1 is hydrogen,
R2 means phenyl group) is obtained in good yield.
アミノ酸の選択により、２位に１―アミノアル
キル基を自由に導入出来る優れた方法と言える。
以下本発明を実施例によつてさらに具体的に説明
する。 This is an excellent method that allows a 1-aminoalkyl group to be freely introduced into the 2-position by selecting the amino acid.
The present invention will be explained in more detail below using Examples.
実施例 １
２―（１―アセトアミノメチル）―６―メチル
―４（3H）―ピリミジノン（一般式、式中
R1は水素、R2はメチル基を意味する）の製法
金属ナトリウム（5.2ｇ、0.23当量）を無水メ
タノール（90ml）にとかし、これに３―アミノク
ロトンアミド（）（4.5ｇ、0.45モル）およびＮ
―アセチルグリシンエチルエステル（一般式、
式中R1は水素、R2はメチル、R3はエチルを意味
する）（13ｇ、0.09モル）をとかし、この混液を
５時間加熱還流する。冷後少量の水を加え、10％
塩酸で中和する、減圧乾固し、残渣をクロロホル
ムで抽出する。Example 1 2-(1-acetaminomethyl)-6-methyl-4(3H)-pyrimidinone (general formula,
Metallic sodium ( 5.2 g, 0.23 equivalents) was dissolved in anhydrous methanol (90 ml), and 3-aminocrotonamide ( ) (4.5 g, 0.45 mol) was dissolved in anhydrous methanol (90 ml). and N
- Acetylglycine ethyl ester (general formula,
In the formula, R 1 is hydrogen, R 2 is methyl, and R 3 is ethyl) (13 g, 0.09 mol) is dissolved and the mixture is heated under reflux for 5 hours. After cooling, add a small amount of water to 10%
Neutralize with hydrochloric acid, dry under reduced pressure, and extract the residue with chloroform.
クロロホルム抽出分より得られる結晶をメタノ
ール・酢酸エチルで再結晶し、mp196―197゜
（dec）の無色針状晶、5.9ｇ（71％）、を得る。 The crystals obtained from the chloroform extract were recrystallized from methanol/ethyl acetate to obtain 5.9 g (71%) of colorless needle crystals with mp 196-197° (dec).
分析値：C8H11N3O2として
計算値：Ｃ，53.03；Ｈ，6.12；Ｎ，23.19
実測値：Ｃ，53.20；Ｈ，6.30；Ｎ，23.00
赤外吸収スペクトル（KBr）：1688，1660，
1610
実施例 ２
２―（１―イソブチリルアミノメチル）―６―
メチル―４（3H）―ビリミジノン（一般式
、式中R1は水素、R2はイソプロピル基を意
味する）の製法
金属ナトリウム（3.5ｇ）を無水メタノール
（60ml）にとかし、これに（３ｇ）およびＮ―
イソブチリルグリシンエチルエステル（一般式
、式中R1は水素、R2はイソプロピル、R3はエ
チル基を意味する）（10.4ｇ）を加え、水浴上８
時間加熱還流する。冷後10％塩酸で中和し、濃縮
乾固し、残渣をクロロホルムで抽出する。これよ
りmp199―201゜（dec）の無色鱗片晶（メタノー
ルより再結晶）、44ｇ（70％）、を得る。 Analytical value: As C 8 H 11 N 3 O 2 Calculated value: C, 53.03; H, 6.12; N, 23.19 Actual value: C, 53.20; H, 6.30; N, 23.00 Infrared absorption spectrum (KBr): 1688, 1660,
1610 Example 2 2-(1-isobutyrylaminomethyl)-6-
Method for producing methyl-4(3H)-pyrimidinone (general formula, in which R 1 means hydrogen and R 2 means isopropyl group) Dissolve metallic sodium (3.5 g) in anhydrous methanol (60 ml), and add (3 g) to this. and N-
Add isobutyrylglycine ethyl ester (general formula, in which R 1 is hydrogen, R 2 is isopropyl, and R 3 is ethyl group) (10.4 g), and heated on a water bath for 8 hours.
Heat to reflux for an hour. After cooling, neutralize with 10% hydrochloric acid, concentrate to dryness, and extract the residue with chloroform. From this, 44 g (70%) of colorless scale crystals (recrystallized from methanol) with mp 199-201° (dec) was obtained.
分析値：C10H15N3O2として
計算値：Ｃ，57.20；Ｈ，7.23；Ｎ，20.08
実測値：Ｃ，57.24；Ｈ，7.28；Ｎ，20.32
赤外吸収スペクトル（KBr）：1670，1635，
1595
実施例 ３
２―（１―ベンズアミノメチル）―６―メチル
―４（3H）―ピリミドン（一般式、式中R1
は水素、R2はフエニル基を意味する）の製法
金属ナトリウム（2.88ｇ）を無水メタノール
（50ml）にとかし、これに（2.5ｇ）および馬尿
酸エチルエステル（一般式、式中R1は水素、
R2はフエニル、R3はエチル基を意味する）（10.35
ｇ）をとかし、水浴上３時間加熱還流する。冷
後、少量の水を加えついで10％塩酸で中和すると
結晶が析出する。これを吸引取し、メタノール
より再結晶してmp230−232゜の無色針状晶、
4.78（79％）、を得る。 Analytical value: As C 10 H 15 N 3 O 2 Calculated value: C, 57.20; H, 7.23; N, 20.08 Actual value: C, 57.24; H, 7.28; N, 20.32 Infrared absorption spectrum (KBr): 1670, 1635,
1595 Example 3 2-(1-benzaminomethyl)-6-methyl-4(3H)-pyrimidone (general formula, in which R 1
is hydrogen, R 2 is phenyl group) Dissolve metallic sodium (2.88 g) in anhydrous methanol (50 ml), add (2.5 g) and hippuric acid ethyl ester (general formula, in which R 1 is hydrogen ,
R 2 means phenyl, R 3 means ethyl group) (10.35
g) and heated under reflux on a water bath for 3 hours. After cooling, add a small amount of water and neutralize with 10% hydrochloric acid to precipitate crystals. This was sucked out and recrystallized from methanol to produce colorless needle-like crystals of mp230-232°.
4.78 (79%), get.
分析値：C13H13N3O2として
計算値：Ｃ，64.18；Ｈ，5.39；Ｎ，17.28
実測値：Ｃ，64.60；Ｈ，5.38；Ｎ，17.32
赤外吸収スペクトル（液膜）：1660，1635，
1600
実施例 ４
２―（１―アセトアミノエチル）―６―メチル
−４（3H）―ピリミジノン（一般式、式中
R1，R2はメチル基を意味する）の製法
金属ナトリウム（0.57ｇ）を無水メタノール
（50ml）にとかし、これに（0.5ｇ）およびＮ―
アセチルアラニンエチルエステル（一般式、式
中R1，R2はメチル、R3はエチル基を意味する）
（1.6ｇ）を加え、７時間加熱還流する。冷後10％
塩酸で中和し、減圧濃縮し、残渣をクロロホルム
で温浸する。クロロホルム溶液を濃縮し、残渣を
メタノール・酢酸エチルで再結晶してmp216―
218゜の無色針状晶、0.55ｇ（36％）、を得る。 Analytical value: As C 13 H 13 N 3 O 2 Calculated value: C, 64.18; H, 5.39; N, 17.28 Actual value: C, 64.60; H, 5.38; N, 17.32 Infrared absorption spectrum (liquid film): 1660 ,1635,
1600 Example 4 2-(1-acetaminoethyl)-6-methyl-4(3H)-pyrimidinone (general formula,
Metallic sodium ( 0.57g ) was dissolved in anhydrous methanol (50ml), and (0.5g ) and N-
Acetylalanine ethyl ester (general formula, where R 1 and R 2 are methyl and R 3 is ethyl group)
(1.6 g) and heated under reflux for 7 hours. 10% after cooling
Neutralize with hydrochloric acid, concentrate under reduced pressure, and digest the residue with chloroform. Concentrate the chloroform solution and recrystallize the residue from methanol/ethyl acetate to obtain mp216-
0.55 g (36%) of colorless needles of 218° are obtained.
分析析値：C9H13N3O2として
計算値：Ｃ，55.37；Ｈ，6.71；Ｎ，21.53
計測値：Ｃ，55.15；Ｈ，6.80；Ｎ，21.59
赤外吸収スペクトル（液膜）：1675，1640，
1601
実施例 ５
２―（１―アセトアミノ―３―メチルブチル）
―６―メチル―４（3H）―ピリミジノン（一
般式、式中R1はイソブチル、R2はメチル基
を意味する）の製法
金属ナトリウム（0.57ｇ）を無水メタノール
（10ml）にとかし、これに（0.5ｇ）およびＮ―
アセチルロイシンエチルエステル（一般式、式
中R1はイソブチル、R2はメチル、R3はエチル基
を意味する）（２ｇ）を加える。混合液を水浴上
４時間加熱還流後、10％塩酸で中和、濃縮乾固す
る。残渣を水洗し、不溶残渣をベンゼンより再結
晶して、mp175―177゜の無色針状晶、0.87ｇ
（67％）、を得る。 Analytical value: C 9 H 13 N 3 O 2 Calculated value: C, 55.37; H, 6.71; N, 21.53 Measured value: C, 55.15; H, 6.80; N, 21.59 Infrared absorption spectrum (liquid film): 1675 ,1640,
1601 Example 5 2-(1-acetamino-3-methylbutyl)
-6-Methyl-4(3H)-pyrimidinone (general formula, in which R 1 means isobutyl and R 2 means methyl group) Metallic sodium (0.57 g) was dissolved in anhydrous methanol (10 ml), and dissolved in this. (0.5g) and N-
Acetylleucine ethyl ester (general formula, where R 1 means isobutyl, R 2 means methyl, and R 3 means ethyl group) (2 g) is added. The mixture was heated under reflux on a water bath for 4 hours, neutralized with 10% hydrochloric acid, and concentrated to dryness. The residue was washed with water, and the insoluble residue was recrystallized from benzene to obtain colorless needle crystals of mp175-177°, 0.87g.
(67%), get.
分析値：C12H19N3O2として
計算値：Ｃ，60.73；Ｈ，8.07；Ｎ，17.71
実測値：Ｃ，60.55；Ｈ，8.10；Ｎ，17.70
赤外吸収スペクトル（液膜）：1660，1645，
1601
実施例 ６
２―（１―ベンズアミノ―３―メチルブチル）
―６―メチル―４（3H）Ｈ―ピリミジノン
（一般式、式中R1はイソブチル、R2はフエニ
ル基を意味する）の製法
金属ナトリウム（5.3ｇ）を無水メタノール
（95ml）にとかし、これに（4.6ｇ）およびＮ―
ベンゾイルロイシンエチルエステル（一般式、
式中R1はイソブチル、R2はフエニル、R3はエチ
ル基を意味する）（24.2ｇ）を加える。この混合
物を水浴上７時間加熱還流する。冷後10％塩酸で
中和し、減圧乾固する。残渣をクロロホルムで温
浸する。クロロホルム溶液を濃縮し、残渣をメタ
ノール、酢酸エチルで再結晶してmp208―209゜
の無色針状晶、9.7ｇ（71％）、得る。 Analytical value: As C 12 H 19 N 3 O 2 Calculated value: C, 60.73; H, 8.07; N, 17.71 Actual value: C, 60.55; H, 8.10; N, 17.70 Infrared absorption spectrum (liquid film): 1660 ,1645,
1601 Example 6 2-(1-benzamino-3-methylbutyl)
-6-Methyl-4(3H)H-pyrimidinone (general formula, in which R 1 means isobutyl and R 2 means phenyl group) Dissolve metallic sodium (5.3 g) in anhydrous methanol (95 ml), (4.6g) and N-
Benzoylleucine ethyl ester (general formula,
In the formula, R 1 is isobutyl, R 2 is phenyl, and R 3 is ethyl group) (24.2 g) is added. The mixture is heated to reflux on a water bath for 7 hours. After cooling, neutralize with 10% hydrochloric acid and dry under reduced pressure. Digest the residue with chloroform. The chloroform solution was concentrated, and the residue was recrystallized from methanol and ethyl acetate to obtain 9.7 g (71%) of colorless needle crystals with a mp of 208-209°.
分析値：C17H21N3O2として
計算値：Ｃ，68.20；Ｈ，7.07；Ｎ，14.04
実測値：Ｃ，68.23；Ｈ，7.15；Ｎ，13.90
赤外級スペクトル（KBr）：1650，1665
実施例 ７
２―（１―アセトアミノ―２―フエニルエチ
ル）―６―メチル―４（3H）―ピリミジノン
（一般式、式中R1はベンジル、R2はメチル基
を意味する）の製法
金属ナトリウム（0.57ｇ）を無水メタノール
（10ml）にとかし、これに（0.5ｇ）およびＮ―
アセチルフエニルアラニンエチルエステル（一般
式、式中R1はベンジル、R2はメチル、R3はエ
チル基を意味する）（2.35ｇ）を加える。混合物
を６時間加熱還流後、10％塩酸で中和する。減圧
濃縮し、さらに水を加え析出する結晶性物質を
取する。エタノールより再結晶してmp210―213
゜の無色針状晶、1.2ｇ（85％）、を得る。 Analytical value: As C 17 H 21 N 3 O 2 Calculated value: C, 68.20; H, 7.07; N, 14.04 Actual value: C, 68.23; H, 7.15; N, 13.90 Infrared class spectrum (KBr): 1650, 1665 Example 7 Process for producing 2-(1-acetamino-2-phenylethyl)-6-methyl-4(3H)-pyrimidinone (general formula, in which R 1 means benzyl and R 2 means methyl group) Sodium metal (0.57 g) was dissolved in anhydrous methanol (10 ml), and this was mixed with (0.5 g) and N-
Add acetylphenylalanine ethyl ester (general formula, where R 1 is benzyl, R 2 is methyl, and R 3 is ethyl group) (2.35 g). The mixture is heated under reflux for 6 hours and then neutralized with 10% hydrochloric acid. Concentrate under reduced pressure and add water to collect the precipitated crystalline substance. Recrystallized from ethanol mp210-213
1.2 g (85%) of colorless needle crystals of .
分析値：C15H17N3O2として
計算値：Ｃ，66.40；Ｈ，6.32；Ｎ，15.49
実測値：Ｃ，66.55；Ｈ，6.50；Ｎ，15.50
赤外吸収スペクトル（液膜）：1675，1655，
1601 Analytical value: As C 15 H 17 N 3 O 2 Calculated value: C, 66.40; H, 6.32; N, 15.49 Actual value: C, 66.55; H, 6.50; N, 15.50 Infrared absorption spectrum (liquid film): 1675 ,1655,
1601
Claims (1)
―アシル―α―アミノ酸エステル（下記一般式
、式中R1は水素、直鎖又は枝分れした低級ア
ルキル基あるいはアラルキル基、R2は低級アル
キル基又はアリール基、さらにR3は低級アルキ
ル基を意味する）とを反応させることを特徴とす
る２―（１―アシルアミノアルキル）―６―メチ
ル―４（3H）―ピリミジノン（下記一般式、
式中R1およびR2は一般式に対応する置換基を
意味する）の製法。 [Claims] 1 3-Aminocrotonamide (formula below) and N
-Acyl-α-amino acid ester (the following general formula, where R 1 is hydrogen, a linear or branched lower alkyl group or an aralkyl group, R 2 is a lower alkyl group or an aryl group, and R 3 is a lower alkyl group) 2-(1-acylaminoalkyl)-6-methyl-4(3H)-pyrimidinone (meaning the following general formula,
In the formula, R 1 and R 2 mean substituents corresponding to the general formula).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11847381A JPS5821669A (en) | 1981-07-30 | 1981-07-30 | Preparation of 2-(1-acylaminoalkyl)-6-methyl-4(3h)- pyrimidinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11847381A JPS5821669A (en) | 1981-07-30 | 1981-07-30 | Preparation of 2-(1-acylaminoalkyl)-6-methyl-4(3h)- pyrimidinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5821669A JPS5821669A (en) | 1983-02-08 |
| JPS6143348B2 true JPS6143348B2 (en) | 1986-09-26 |
Family
ID=14737538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11847381A Granted JPS5821669A (en) | 1981-07-30 | 1981-07-30 | Preparation of 2-(1-acylaminoalkyl)-6-methyl-4(3h)- pyrimidinone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5821669A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63263021A (en) * | 1987-04-22 | 1988-10-31 | 三和シヤツタ−工業株式会社 | Roof sprinkler structure in cultivation greenhouse |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100374449B1 (en) * | 1994-03-07 | 2003-09-06 | 가부시끼가이샤 하야시바라 세이부쓰 가가꾸 겐꾸조 | DNA encoding enzymes, recombinant DNA (DNA) and enzymes, transformants and methods of making them |
| RU2004135554A (en) * | 2002-05-09 | 2006-01-20 | Цитокинетикс, Инк. (Us) | Pyrimidinones, compositions based on them and methods for their use |
| EP1509507A4 (en) * | 2002-05-23 | 2006-09-13 | Merck & Co Inc | INHIBITORS OF MITOTIC KINESIN |
-
1981
- 1981-07-30 JP JP11847381A patent/JPS5821669A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63263021A (en) * | 1987-04-22 | 1988-10-31 | 三和シヤツタ−工業株式会社 | Roof sprinkler structure in cultivation greenhouse |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5821669A (en) | 1983-02-08 |
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