Ammonium formate → (S)-N-methyl-N-(piperidin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Participants

Reaction Steps

To a solution of (S)—N-(1-benzylpiperidin-3-yl)-N-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (540 mg, 1.19 mmol) in McOH under nitrogen, 10% Pd/C (540 mg) was added. To this suspension, ammonium formate (752 mg, 11.9 mmol) was added and the reaction mixture was refluxed under nitrogen for 4 h. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to rt and filtered over celite. The filtrate was concentrated in vacuo to give a residue that was purified by column chromatography (silica gel, gradient EtOAc in hexanes) to afford the titled intermediate (325 mg, 80%). 1H NMR (400 MHz, CD3OD): δ 8.34 (s, 1H), 8.29 (s, 1H), 5.70 (s, 2H), 3.63 (t, J=8.4 Hz, 2H), 3.39 (s, 3H), 3.22 (m, 2H), 3.03 (m, 1H), 2.11 (m, 1H), 2.00 (m, 1H), 1.32 (m, 4H), 0.87 (t, J=8.4 Hz, 2H), 0.00 (9H). LC-MS: m/z [M+1]=363.

Provenance & Evidence