Tetrabutylammonium Fluoride → (2S)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-cyanopyridin-2-yl)-3-(2-hydroxyethoxy)propanamide

Participants

Reaction Steps

Tetrabutylammonium fluoride (1M in THF) (0.139 mL, 0.14 mmol) was added to (2S)-3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-cyanopyridin-2-yl)propanamide (Intermediate AB1) (100 mg, 0.14 mmol) in THF (2 mL) under nitrogen. The resulting mixture was stirred at ambient temperature for 1 hour. The reaction mixture was quenched with saturated NH4Cl (1 mL), diluted with DCM (10 ml) and poured onto a phase separator. The organic layer was collected and evaporated. The residue was purified by flash silica chromatography, eluting with 0 to 100% ethyl acetate in isohexane to afford the product (38.0 mg, 56.8%). 1H NMR (300 MHz, CDCl3) δ 2.36 (1H, s), 3.70-3.86 (4H, m), 4.16-4.27 (2H, m), 6.07 (1H, t), 7.45-7.52 (1H, m), 7.93-8.05 (2H, m), 8.32-8.38 (1H, m), 8.46 (1H, s), 8.55-8.58 (1H, m), 8.60-8.65 (2H, m), 9.28 (1H, s). m/z (ES+) (M+H)+=481.31; HPLC tR=1.63 min.

Provenance & Evidence