Sodium hydride → HCID 118318867, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-(but-3-en-1-yl)-4-fluorophenyl)methanol (43.8 mg, 0.243 mmol) and (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(iodomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (142 mg, 0.243 mmol) in DMF (5 mL) at 0° C. was added NaH (9.72 mg, 0.243 mmol) and the reaction was stirred at 0° C. for 3 h. It was 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 20% EtOAc/hexane to isolate (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(((2-(but-3-en-1-yl)-4-fluorobenzyl)oxy)methyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (50 mg, 0.079 mmol, 32.3% yield) as an oil. LCMS (M+1)=637.3.

Provenance & Evidence