Tetrabutylammonium Fluoride → (S)-ethyl 2-(tert-butoxy)-2-(2-(3-(3,5-difluoro-2-hydroxyphenyl)propyl)-7-(4-(((R)-5-hydroxyhexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

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-(3,5-difluoro-2-hydroxyphenyl)propyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (130 mg, 0.142 mmol) in THF (3 mL) was added 1M solution of TBAF (0.712 mL, 0.712 mmol) and the resulting mixture was stirred at room temp for 16 h. Mixture was then concentrated and the residue was purified by Biotage (5-50% EtOAc/hexane) to afford (S)-ethyl 2-(tert-butoxy)-2-(2-(3-(3,5-difluoro-2-hydroxyphenyl)propyl)-7-(4-(((R)-5-hydroxyhexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (70 mg, 0.104 mmol, 72.9% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 6.79-6.61 (m, 2H), 6.34 (s, 1H), 5.94 (br. s., 1H), 4.29-4.09 (m, 2H), 3.87 (d, J=5.4 Hz, 1H), 3.49-3.36 (m, 2H), 2.92-2.79 (m, 3H), 2.76 (br. s., 1H), 2.62 (s, 3H), 2.16-2.07 (m, 2H), 1.98 (d, J=13.2 Hz, 2H), 1.64 (d, J=4.3 Hz, 3H), 1.56-1.41 (m, 4H), 1.33 (br. s., 2H), 1.27-1.20 (m, 15H). LCMS (M+H)=675.8.

Provenance & Evidence