Tetrabutylammonium Fluoride → HCID 57504441, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (1M in THF) (1.376 mL, 1.38 mmol) was added to (2S)-5-(tert-butyldimethylsilyloxy)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-cyanopyridin-2-yl)pentanamide (Intermediate AW2) (797 mg, 1.38 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 (166 mg, 25.9%, 100% ee). 1H NMR (400 MHz, CDCl3) δ 1.61 (1H, t), 1.81-1.92 (2H, m), 2.22-2.40 (2H, m), 3.76-3.88 (2H, m), 5.95 (1H, t), 7.45-7.50 (1H, m), 7.93-7.98 (1H, m), 7.99-8.04 (1H, m), 8.35-8.41 (1H, m), 8.44 (1H, s), 8.53-8.57 (1H, m), 8.60-8.64 (2H, m), 9.03 (1H, s); m/z (ES−) (M−H)−=463.37; HPLC tR=1.68 min.

Provenance & Evidence