Sodium hydride → 7-[4-(4-Chlorobenzoyl)benzyl]-3-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 1291398

반응식

HRID 1291398 반응식
[CH:1]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][NH:13][C:7]=2[N:6]=[CH:5]1)([CH3:3])[CH3:2].[H-].[Na+].[Cl:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1>COCCOC>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27][N:13]3[C:7]4[N:6]=[CH:5][N:4]([CH:1]([CH3:3])[CH3:2])[C:9](=[O:10])[C:8]=4[CH:11]=[CH:12]3)=[CH:25][CH:24]=2)=[O:22])=[CH:31][CH:32]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 189190403-Isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

생성물 1

HCID 189188667-[4-(4-Chlorobenzoyl)benzyl]-3-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-one수율 88.8%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

실험 절차

Under argon gas, 3-isopropyl-7H-pyrrolo[2,3-d]-pyrimidin-4-one (89 mg) was dissolved in anhydrous DME (2 ml) and, under ice-cooling and stirring, 60% sodium hydride-oil (22 mg) was added. The mixture was stirred for 30 minutes, after which a solution of 4-(4-chlorobenzoyl)benzyl bromide (201 mg) in anhydrous DME (1 ml) was added. Then, the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by flash column chromatography (silica gel, 12 g; hexane: ethyl acetate =4:1-3:2) to provide the title compound as colorless powder (181 mg).

후처리

  1. temperaturecooling
  2. stirringThe mixture was stirred for 30 minutes
  3. stirringThen, the mixture was stirred at room temperature for 2 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure
  9. customthe residue was purified by flash column chromatography (silica gel, 12 g; hexane: ethyl acetate =4:1-3:2)

출처 및 근거

ORD 기록
ord-a1aa45ffbd484eaaa858da39786848ea
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753664

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