Sodium hydride → HCID 118318873, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (3-allylphenyl)methanol (33.0 mg, 0.222 mmol) in DMF (3 mL) at 0° C. was added (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(iodomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (130 mg, 0.222 mmol) and NaH (8.90 mg, 0.222 mmol). The reaction mixture was stirred at 0° C. for 2 h. It was then diluted 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-(((3-allylbenzyl)oxy)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (50 mg, 0.083 mmol, 37.2% yield) as an oil. LCMS (M+1)=605.4.

Provenance & Evidence