Phosphate → HCID 86652263, compound

Participants

Reaction Steps

4-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide (4F, 3.9 g, 1.0 equivalent) was dissolved in THF (0.13 M) and treated with TBAF (1.0 M in THF, 4.0 equivalents). After 60 hours, pH 7 phosphate buffer was added and the mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by chromatography (SiO2, gradient of 25 to 50% EtOAc/hexanes) to give N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide (4G) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (s, 6H), 2.44 (s, 3H), 3.46 (d, J=5.05 Hz, 2H), 4.76 (t, J=5.31 Hz, 1H), 6.45 (s, 1H), 7.52 (d, J=8.59 Hz, 2H), 7.99 (d, J=8.59 Hz, 2H), 8.06 (s, 1H), 11.30 (s, 1H).

Provenance & Evidence