Tetrabutylammonium Fluoride → HCID 123712807, compound

Participants

Reaction Steps

To a solution of (S)-ethyl 2-(tert-butoxy)-2-(7-(4-(((R)-5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidin-1-yl)-2-(3-(4-fluoro-2-hydroxyphenyl)prop-1-en-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (380 mg, 0.425 mmol) in THF (5 mL) was added TBAF 1M in THF (0.851 mL, 0.851 mmol) and the resulting mixture was stirred at room temp for 16 h. At this point LCMS indicated approx 70% conversion so another 1 equiv of TBAF was added and the mixture was stirred for another 5 h. At this point LCMS indicated completion of reaction. Mixture was then concentrated and purified by biotage (5-30% EtOAc/hexane) to afford (S)-ethyl 2-(tert-butoxy)-2-(2-(3-(4-fluoro-2-hydroxyphenyl)prop-1-en-1-yl)-7-(4-(((R)-5-hydroxyhexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (240 mg, 0.367 mmol, 86% yield) as approx 2:1 mixture of isomers. LCMS (M+H)=655.3.

Provenance & Evidence