Aluminium lithium hydride → 2-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-ethanol
Reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[C:14]([CH2:24][CH3:25])=[N:15][N:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18][C:17]=23)=[CH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:24]([C:14]1[C:13]([CH2:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][OH:2])=[CH:11][CH:10]=2)=[C:17]2[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]2[N:15]=1)[CH3:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-acetic acid methyl ester (9) (1.2 g, 3.40 mmol) was dissolved in 36 ml of THF. LiAlH4 (1.867 ml, 3.73 mmol) was added slowly to the reaction mixture and stirring was continued for 3 h at rt. The mixture was quenched with water and washed twice with CH2 Cl2. The aqueous layer was acidified with 1N HCl to pH3 and three times extracted with CH2 Cl2. The combined organic layers were washed with water and NaCl-solution, dried over Na2 SO4 and evaporated. The product was purified by chromatography (silica gel, chexane/ethylacetate).