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

HRID 1786848
ノート
印刷プレビュー

反応式

HRID 1786848 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 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

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ef295f3049624ba9a6f932b5d9010853
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07507740B2

反応ノート

読み込み中…

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