Pyridine → N-[3-(dimethylamino)phenyl]-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide

HRID 1631552ノート

反応式

HRID 1631552 の反応式
N1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.[CH3:19][N:20]([CH3:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=1.[N:29]1([C:35]2[N:36]=[C:37]([CH2:42][C:43]([O-])=[O:44])[NH:38][C:39](=[O:41])[CH:40]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[Na+]>CN(C)C=O.ClCCl.C(OCC)C.CO>[CH3:19][N:20]([CH3:28])[C:21]1[CH:22]=[C:23]([NH:27][C:43](=[O:44])[CH2:42][C:37]2[NH:38][C:39](=[O:41])[CH:40]=[C:35]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:36]=2)[CH:24]=[CH:25][CH:26]=1

参加物

9

反応物 4

HCID 1049PyridineHCID 76084N,N-dimethyl-m-phenylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

生成物 1

HCID 136041849N-[3-(dimethylamino)phenyl]-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide収率 8.8%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

0.160 ml of pyridine, 240 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 400 mg of N,N-dimethyl-m-phenylenediamine are added to a solution of 250 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 2 of Example 1 in 4 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature overnight and is then concentrated under reduced pressure. Water and ethyl acetate are added and the resulting mixture is thus stirred for 30 minutes. The precipitate formed is filtered off, rinsed with ethyl ether and dried in a rotary evaporator. After purification by silica column chromatography as a solid deposit, eluent: dichloromethane/methanol 95/05, a solid is obtained which is taken up in a mixture of dichloromethane, methanol and ethyl ether. The solid is filtered off and dried. 30 mg of N-[3-(dimethylamino)phenyl]-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the form of a yellow solid, the characteristics of which are the following:

後処理

  1. concentrationis then concentrated under reduced pressure
  2. additionWater and ethyl acetate are added
  3. stirringthe resulting mixture is thus stirred for 30 minutes
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed with ethyl ether
  7. customdried in a rotary evaporator
  8. customAfter purification by silica column chromatography as a solid deposit, eluent
  9. customdichloromethane/methanol 95/05, a solid is obtained which
  10. filtrationThe solid is filtered off
  11. customdried

出典と根拠

ORDレコード
ord-6b98542af6b0495494d77c25d9689bb4
出典データセット
uspto-grants-2014_07
特許番号
US08791255B2

反応ノート

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