Tetrahydrofuran → {1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazol-4-yl}-methanol
Reaction equation
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]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
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.
Workup
- customThe mixture was quenched with water
- additiondiluted with dichloromethane
- filtrationThe mixture was filtrated
- extractionextracted with dichloromethane
- washOrganic layer was washed with water and brine
- customdried over Na2 SO4
- concentrationconcentrated
- customto afford a yellow foam
- customThe product was used in the next step without further purification
Sources & evidence
- ORD record
- ord-fb0718b54a004c9486072111d3c999c2
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748435B2
Reaction notes
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