Sodium Hydroxide → HCID 59513826, compound

Participants

Reaction Steps

To a solution of 5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-3-[2-(methylsulfonyl)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine (3.00 g, 5.56 mmol) in DCM (90 mL) and ethanol (90 mL), NaBH4 (526 mg, 13.9 mmol) was added one portion at rt. The mixture was stirred at rt for 1 h. The reaction mixture was poured into aq. 1N NaOH and extracted with DCM. The organic layer was combined, washed with brine and dried (Na2SO4). The solvent was evaporated under reduced pressure. Chromatography on silica gel eluting with DCM/EtOAc gradient (0-20% EtOAc) gave a pale yellow solid (1.87 g).

Provenance & Evidence