Ammonium formate → HCID 178481007, compound

Participants

Reaction Conditions

Reaction Steps

A solution of trans-3-[4-(benzyloxy)phenyl]-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.806 g, 1.62 mmol) in absolute ethanol (40 mL) was treated with palladium 10 wt. % on activated carbon (0.161 g, 0.324 mmol) and ammonium formate (0.511 g, 8.1 mmol). The reaction mixture was stirred at 80° C. for 3 h, very little product was seen by thin layer chromatography. Palladium 10 wt. % on activated carbon (0.161 g, 0.324 mmol) was added and stirred for an additional hour, still very little product detected. Ammonium formate (0.204 g, 3.24 mmol) was added and stirred over night. The reaction mixture was filtered through a pad of celite, which was washed with ethanol (500 mL). The organic layer was removed under reduced pressure. The resulting solid was triturated with ethyl acetate, and dried over night under high vacuum to give 0.491 g (75%) of trans-4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenol. 1H NMR (DMSO-d6, 400 MHz) δ 9.74 (s, 1H), 8.2 (s, 1H), 7.46-7.44 (d, 2H, J=8 Hz), 6.92-6.90 (d, 2H, J=8 Hz), 4.64-4.58 (m, 1H), 2.67-2.50 (m, 5H), 2.39-2.34 (m, 4H), 2.17 (s, 3H), 2.06-1.92 (m, 6H), 1.50-1.42 (m, 2H); HPLC Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt 3.337 min (96%).

Provenance & Evidence