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Sodium hydride → methyl 4-{[7-(methylthio)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]methyl}benzoate

HRID 1786848
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HRID 1786848 반응식
[CH3:1][S:2][C:3]1[C:4]2[NH:11][N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[H-].[Na+].Br[CH2:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23]C)=[O:21])=[CH:18][CH:17]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[C:4]2[N:11]([CH2:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)[N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[CH3:1][S:2][C:3]1[C:4]2[C:5](=[CH:9][N:10]([CH2:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)[N:11]=2)[N:6]=[CH:7][N:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 552958947-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine

생성물 2

HCID 67520953methyl 4-{[7-(methylthio)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]methyl}benzoateHCID 67521447methyl 4-{[7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]methyl}benzoate

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (400 mg) in N,N-dimethylformamide (8 mL) was added 60% sodium hydride (98 mg) under ice-cooling, and the mixture was stirred at room temperature for 10 min. Then, ethyl 4-(bromomethyl)benzoate (606 mg) was added under ice-cooling, and the mixture was stirred at room temperature for 30 min. After the completion of the reaction, the mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1→1:2) to give methyl 4-{[7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]methyl}benzoate (251 mg) and methyl 4-{[7-(methylthio)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]methyl}benzoate (450 mg) both as pale-yellow solids.

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 30 min
  4. customAfter the completion of the reaction
  5. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  6. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ef295f3049624ba9a6f932b5d9010853
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07507740B2

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