Sodium hydride → HCID 118318890, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(iodomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (200 mg, 0.342 mmol) and (2-allyl-4,5-difluorophenyl)methanol (63.0 mg, 0.342 mmol) in DMF (2 mL) at 0° C. was added NaH (13.69 mg, 0.342 mmol). It was stirred at 0° C. for 2 h, then quenched with water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 25% EtOAc/hexane to obtain (S)-ethyl 2-(2-(((2-allyl-4,5-difluorobenzyl)oxy)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (100 mg, 43.6%) as an oil. LCMS (M+1)=641.5.

Provenance & Evidence