Ammonium Chloride → HCID 46175430, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (1M in THF) (5.96 mL, 5.96 mmol) was added to (2S)-3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-N-(5-chloropyridin-2-yl)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide (Intermediate AD1) (3.67 g, 5.96 mmol) in THF (75 mL) under nitrogen. The resulting mixture was stirred at ambient temperature for 20 hours, saturated ammonium chloride (50 mL) added, diluted with DCM (100 mL) and poured onto a phase separator. The organic layer was evaporated and the crude product was purified by flash silica chromatography, eluting with 0 to 10% MeOH in EtOAc to afford the product (1.7 g, 57%). 1H NMR (400 MHz, DMSO) δ 2.95-3.10 (3H, m), 3.10-3.15 (1H, m), 3.60-3.70 (2H, m), 4.14-4.21 (1H, m), 5.26 (1H, d), 5.73-5.75 (1H, m), 7.74 (1H, dd), 7.88 (1H, dd), 8.01-8.07 (1H, m), 8.33 (1H, dd), 8.39-8.40 (1H, m), 8.55 (1H, s), 8.66 (1H, s), 8.68 (1H, dd), 11.13 (1H, s); m/z (ESI+) (M+H)+=501; HPLC tR=1.27 min.

Provenance & Evidence