Water → (+/-)-9-(2,3-Dihydro-benzofuran-2-ylmethyl)-7,7-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

HRID 2375326노트

반응식

HRID 2375326 반응식
CC1(C)CN2C(=[O:17])C=C(C3C=CN=CC=3)N=C2NC1.[H-].[Na+].N1[C:30]2[CH2:29][C@H:28]([CH2:31][N:32]3[C:37]4=[N:38][C:39]([C:43]5[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=5)=[CH:40][C:41](=[O:42])[N:36]4[CH2:35][C:34]([CH3:50])([CH3:49])[CH2:33]3)[CH2:27][C:26]=2[CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[O:17]1[C:30]2[CH:29]=[CH:23][CH:24]=[CH:25][C:26]=2[CH2:27][CH:28]1[CH2:31][N:32]1[C:37]2=[N:38][C:39]([C:43]3[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=3)=[CH:40][C:41](=[O:42])[N:36]2[CH2:35][C:34]([CH3:49])([CH3:50])[CH2:33]1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12073797(+)-(6R)-9-(6,7-Dihydro-5H-[1]pyrindin-6-ylmethyl)-7,7-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-oneHCID 1357386167,7-Dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

생성물 1

HCID 12073800(+/-)-9-(2,3-Dihydro-benzofuran-2-ylmethyl)-7,7-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one수율 22%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
40 °C

실험 절차

A suspension of 0.51 g (2 mmol) of 7,7-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one in 10 ml of anhydrous dimethylformamide was treated with 96 mg (2 mmol) of sodium hydride (50% suspension in mineral oil) and the resulting mixture was stirred at 40° C. for 40 min. 0.52 g (2 mmol) of (+/−)2-iodomethyl-2,3-dihydro-benzofuran (prepared according to Synthesis 1997, (1), 23-25) in 2 ml of anhydrous dimethylformamide was added and the reaction mixture stirred at 60° C. for 20 min. The solution was treated with water and extracted with ethyl acetate. The organic phase was dried and evaporated to give crude product, which was purified by silica gel chromatography, eluting with dichloromethane/methanol/ammonia in the proportions 99/1/0.1 to 98/2/0.2 to give 0.171 g of pure product obtained in the form of free base. Mp: 147-149° C.

후처리

  1. stirringthe reaction mixture stirred at 60° C. for 20 min
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. customevaporated
  5. customto give crude product, which
  6. customwas purified by silica gel chromatography
  7. washeluting with dichloromethane/methanol/ammonia in the proportions 99/1/0.1 to 98/2/0.2

출처 및 근거

ORD 기록
ord-3ae3c9d82e9347b79ba211e4860fef88
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465737B2

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