Tetrahydrofuran → {1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazol-4-yl}-methanol

HRID 403494ノート

反応式

HRID 403494 の反応式
C([O:3][C:4]([C:6]1[C:7]([CH3:31])=[N:8][N:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]3[C:19]([CH2:29][CH3:30])=[N:20][N:21]4[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[N:23][C:22]=34)=[CH:13][CH:12]=2)[CH:10]=1)=O)C.CC(C[AlH]CC(C)C)C.C1COCC1>ClCCl>[CH2:29]([C:19]1[C:18]([CH2:17][C:14]2[CH:15]=[CH:16][C:11]([N:9]3[CH:10]=[C:6]([CH2:4][OH:3])[C:7]([CH3:31])=[N:8]3)=[CH:12][CH:13]=2)=[C:22]2[N:23]=[C:24]([CH3:28])[CH:25]=[C:26]([CH3:27])[N:21]2[N:20]=1)[CH3:30]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 683789781-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

生成物 1

HCID 68378977{1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazol-4-yl}-methanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-70 °C

実験手順

1-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (17) (618 mg, 1.53 mmol) was dissolved in 10 ml of dichloromethane and cooled at −70° C. A 1M solution of DIBAH in THF (3.1 ml, 3.1 mmol) was added and the reaction mixture was stirred for 2 h at −70° C. The mixture was quenched with water and diluted with dichloromethane. The mixture was filtrated and extracted with dichloromethane. Organic layer was washed with water and brine, dried over Na2 SO4 and concentrated to afford a yellow foam. The product was used in the next step without further purification.

後処理

  1. customThe mixture was quenched with water
  2. additiondiluted with dichloromethane
  3. filtrationThe mixture was filtrated
  4. extractionextracted with dichloromethane
  5. washOrganic layer was washed with water and brine
  6. customdried over Na2 SO4
  7. concentrationconcentrated
  8. customto afford a yellow foam
  9. customThe product was used in the next step without further purification

出典と根拠

ORDレコード
ord-fb0718b54a004c9486072111d3c999c2
出典データセット
uspto-grants-2014_06
特許番号
US08748435B2

反応ノート

読み込み中…