Tetrabutylammonium Fluoride → HCID 178447114, compound

Participants

Reaction Steps

To a solution of tert-butyl-[2-[(3S)-3-[(1R)-1,2-dimethyl-1-trimethylsilyloxy-propyl]piperazin-1-yl]-3,5-difluoro-6-(1H-pyrazolo[3,4-d]pyrimidin-3-yl)-4-pyridyl]-dimethyl-silane (134 mg, 0.23 mmol) in THF (3 mL) was added TBAF (1M in THF) (499.8 μL of 1 M, 0.50 mmol) and stirred at ambient temperature for 1 hour. After this time, the reaction mixture was diluted with EtOAc and the organics were washed with water (×3), brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 5 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min] The fractions were isolated and TFA was removed using PS-carbonate cartridge and freeze-dried to give the title compound as an off-white solid (38 mg, 40.2% Yield). H1 NMR (400.0 MHz, DMSO) δ 9.74 (s, 1H), 9.05 (s, 1H), 7.96 (dd, 1H), 4.15 (br s, 1H), 4.01 (d, 1H), 3.76 (d, 1H), 3.11 (d, 1H), 2.85 (d, 2H), 2.77-2.70 (m, 2H), 1.80 (quintet, 1H), 1.05 (s, 3H), 0.89 (d, 3H) and 0.84 (d, 3H) ppm; MS (ES+) 404.2.

Provenance & Evidence