Tetrabutylammonium Fluoride → HCID 57504440, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (1M in THF) (1.177 mL, 1.18 mmol) was added to (2S)-5-(tert-butyldimethylsilyloxy)-N-(5-chloropyridin-2-yl)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)pentanamide (Intermediate AW1) (693 mg, 1.18 mmol) in THF (5 mL) under nitrogen. The resulting mixture was stirred at ambient temperature for 1 hour. The reaction mixture was quenched with saturated NH4Cl (2 mL), diluted with DCM (25 mL) and poured onto a phase separator. The organic layer was loaded onto a silica column and purified by flash silica chromatography, elution gradient 50 to 100% EtOAc in isohexane to afford the product (171 mg, 30.6%, 95% ee). 1H NMR (400 MHz, CDCl3) δ 1.59 (1H, t), 1.81-1.91 (2H, m), 2.21-2.39 (2H, m), 3.73-3.86 (2H, m), 5.95 (1H, t), 7.44-7.50 (1H, m), 7.64-7.72 (1H, m), 7.98-8.04 (1H, m), 8.20-8.27 (2H, m), 8.44 (1H, s), 8.59-8.65 (2H, m), 8.72 (1H, s); m/z (ES+) (M+H)+=474.36; HPLC tR=1.89 min.

Provenance & Evidence