Dimethyl Sulfoxide → 6-Ethyl-1-[4-(4-hydroxybenzoyl)benzyl]-7-methyl-imidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1291385노트

반응식

HRID 1291385 반응식
[CH2:1]([C:3]1[C:8](=[O:9])[N:7]2[CH:10]=[CH:11][NH:12][C:6]2=[N:5][C:4]=1[CH3:13])[CH3:2].[Si]([O:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>CN(C=O)C>[CH2:1]([C:3]1[C:8](=[O:9])[N:7]2[CH:10]=[CH:11][N:12]([CH2:32][C:31]3[CH:30]=[CH:29][C:28]([C:26](=[O:27])[C:25]4[CH:36]=[CH:37][C:22]([OH:21])=[CH:23][CH:24]=4)=[CH:35][CH:34]=3)[C:6]2=[N:5][C:4]=1[CH3:13])[CH3:2]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 18918912HCID 18918912, 화합물HCID 178436760HCID 178436760, 화합물

생성물 1

HCID 189189466-Ethyl-1-[4-(4-hydroxybenzoyl)benzyl]-7-methyl-imidazo[1,2-a]pyrimidin-5(1H)-one수율 10.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 6-ethyl-7-methylimidazo[1,2-a]-pyrimidin-5(1H)-one (3.93 g), 4-(4-t-butyldimethylsilyloxybenzoyl)benzyl bromide (14.79 g) and potassium carbonate (5.97 g) in DMF (25 ml)-dimethyl sulfoxide (25 ml) was stirred at room temperature for 20 hours. This reaction mixture was concentrated and the residue was extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (dichloromethane: methanol =9:1) and recrystallized from ethanol-ethyl acetate to provide the title compound as colorless solid (909 mg).

후처리

  1. concentrationThis reaction mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (dichloromethane: methanol =9:1)
  7. customrecrystallized from ethanol-ethyl acetate

출처 및 근거

ORD 기록
ord-ce19d69685834beca3632b89a35c6d89
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753664

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