Acetonitrile → Ethyl 3-methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]butanoate

HRID 44926

反応式

HRID 44926 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1.[C:23]([OH:28])(=[O:27])[CH:24]=[CH:25][CH3:26].[CH2:29]1CCN2C(=NCCC2)C[CH2:30]1.[C:40](#N)C>>[CH3:26][C:25]([N:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1)([CH3:40])[CH2:24][C:23]([O:28][CH2:29][CH3:30])=[O:27]

参加物

5

反応物 4

HCID 6342AcetonitrileHCID 194992-Butenoic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 426313464-(1H-Pyrazol-4-yl)-7-(2-(trimethylsilyl)ethoxy)methyl-7 H-pyrrolo(2,3-d)-pyrimidine

生成物 1

HCID 66597630Ethyl 3-methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]butanoate収率 91%

実験手順

A solution of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (12.1 g, 0.0384 mol), 2-butenoic acid, 3-methyl-, ethyl ester (16.0 mL, 0.115 mol) and DBU (14.3 mL, 0.0959 mol) in ACN (100 mL) was heated at reflux for 3.5 hours. The solvent was removed in vacuo. The residue was diluted with water, extracted with ethyl acetate, and the combined organic extracts were washed with saturated ammonium chloride, dried over sodium sulfate, and concentrated. The crude residue was purified by flash column chromatography (ethyl acetate/hexanes) to yield the desired product (15.5 g, 91%).

後処理

  1. temperatureat reflux for 3.5 hours
  2. customThe solvent was removed in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washthe combined organic extracts were washed with saturated ammonium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography (ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-b11fff147ad14f93835b89a5ef7ad466
出典データセット
uspto-grants-2013_09
特許番号
US08541425B2

関連ノート

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