(Trimethylsilyl)imidazole → HCID 178447658, compound

Participants

Reaction Conditions

Reaction Steps

tert-butyl-dimethyl-[2,3,5-trifluoro-6-(1H-pyrazolo[3,4-d]pyrimidin-3-yl)-4-pyridyl]silane (170 mg, 0.42 mmol), (2R)-3-methyl-2-[(2S)-piperazin-2-yl]butan-2-ol (109.8 mg, 0.64 mmol), imidazol-1-yl-trimethyl-silane (297.9 mg, 310.3 μL, 2.12 mmol) were dissolved in THF (420 μL). The reaction mixture was heated at 90° C. for 2 days under sealed tube conditions. After this time, the reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc, washed with saturated aqueous NaHCO3, water, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude mixture was purified by column chromatography (ISCO Companion™, 24 g column, eluting with 1-5% NH4OH:MeOH (1:9)/DCM) to give the sub title compound as cream solid 134 mg, 53.5% Yield). H1 NMR (400 MHz, DMSO) δ 14.26 (H, d), 9.66 (H, s), 8.97 (H, s), 3.82 (H, d), 3.60 (H, d), 3.06 (H, dd), 3.72 (4H, m), 1.75 (2H, m), 1.10 (3H, d), 0.80 (15H, m), 0.35 (6H, s) and 0.00 (9H, s).

Provenance & Evidence