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

HRID 403494노트

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HRID 403494 반응식
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]

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb0718b54a004c9486072111d3c999c2
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748435B2

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