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Sodium borohydride → HCID 86672123、化合物

HRID 82274
ノート
印刷プレビュー

反応式

HRID 82274 の反応式
C[O:2][C:3]([C:5]1([N:8]2[C:12]3[N:13]=[CH:14][N:15]=[CH:16][C:11]=3[CH:10]=[CH:9]2)[CH2:7][CH2:6]1)=O.[BH4-].[Na+]>C(O)C>[N:13]1[C:12]2[N:8]([C:5]3([CH2:3][OH:2])[CH2:6][CH2:7]3)[CH:9]=[CH:10][C:11]=2[CH:16]=[N:15][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 708174621-Pyrrolo[2,3-d]pyrimidin-7-yl-cyclopropanecarboxylic acid methyl ester

生成物 1

HCID 86672123HCID 86672123、化合物収率 47%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of 1-Pyrrolo[2,3-d]pyrimidin-7-yl-cyclopropanecarboxylic acid methyl ester (Preparation 246, 610 mg, 2.80 mmol) in ethanol (15 mL) was added sodium borohydride (318.7 mg, 8.42 mmol) and the mixture heated to reflux for 16 hours. The reaction mixture was quenched with water (5 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with water (5 mL), brine (5 mL), dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of DCM:methanol 100:0 to 98:2) to afford the title compound as a light yellow solid in 47% yield, 250 mg.

後処理

  1. temperaturethe mixture heated
  2. temperatureto reflux for 16 hours
  3. customThe reaction mixture was quenched with water (5 mL)
  4. extractionextracted with EtOAc (3×10 mL)
  5. washThe combined organic layers were washed with water (5 mL), brine (5 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe crude material was purified by column chromatography on silica gel (gradient of DCM:methanol 100:0 to 98:2)

出典と根拠

ORDレコード
ord-b852999f622e46e1b0373ad9d7a7b33b
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846698B2

反応ノート

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