Tetrabutylammonium Fluoride → HCID 46175517, compound

Participants

Reaction Steps

A solution of tetrabutylammonium fluoride (1M in THF) (0.891 mL, 0.89 mmol) was added in one portion to a stirred solution of (2S)-2-(1-(2-chloro-6-cyanophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-chloropyridin-2-yl)-3-((R)-1-(triisopropylsilyloxy)propan-2-yloxy)propanamide (Intermediate AY1) (610 mg, 0.89 mmol) in tetrahydrofuran (15 mL). The resulting solution was stirred at ambient temperature for 30 minutes. The reaction mixture was quenched with saturated NH4Cl (10 mL), and diluted with water (20 mL) and EtOAc (70 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (70 mL), The combined organics were dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 50 to 80% EtOAc in isohexane to afford the product (281 mg, 59.7%). 1H NMR (400 MHz, DMSO) δ 1.07 (3H, d), 3.33 (1H, q), 3.40-3.46 (1H, m), 3.61-3.69 (1H, m), 4.09-4.16 (2H, m), 4.57 (1H, t), 5.90 (1H, s), 7.87-7.91 (2H, m), 8.01-8.05 (1H, m), 8.16-8.19 (2H, m), 8.40-8.41 (1H, m), 8.61 (1H, s), 8.78 (1H, t), 11.17 (1H, d); m/z (ES−) (M−H)−=526; HPLC tR=2.94 min.

Provenance & Evidence