Tetrabutylammonium Fluoride → HCID 57504493, compound

Participants

Reaction Steps

A solution of tetrabutylammonium fluoride 2M in THF (0.449 mL, 0.45 mmol) was added in one portion to a stirred solution of (2S)-5-(tert-butyldimethylsilyloxy)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-methylpyridin-2-yl)pentanamide (Intermediate O1) (170 mg, 0.30 mmol) in THF (5 mL). The resulting solution was stirred at ambient temperature for 4 hours, evaporated and the residue dissolved in ethyl acetate (30 mL). This was washed with water (20 mL) and brine (20 mL), dried (MgSO4) and evaporated. The residue was purified by flash silica chromatography, eluting with 0 to 10% MeOH in ethyl acetate to afford the product (100 mg, 73%). 1H NMR (400 MHz, CDCl3) δ 1.61-1.68 (1H, m), 1.84-1.88 (2H, m), 2.23-2.36 (2H, m), 2.30 (3H, s), 3.72-3.82 (2H, m), 5.94-5.98 (1H, m), 7.46 (1H, dd), 7.54 (1H, dd), 8.01 (1H, dd), 8.08-8.10 (1H, m), 8.12-8.15 (1H, m), 8.45 (1H, s), 8.61-8.62 (2H, m), 8.63 (1H, s); m/z (ESI+)(M+H)+=454; HPLC tR=1.51 min.

Provenance & Evidence