Hydrochloric Acid → HCID 118890620, compound

Participants

Reaction Steps

To a solution of compound (S)-tert-butyl 3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)piperidine-1-carboxylate (1 g, 2.22 mmol) in dioxane (10 mL) at 0° C., was added a solution of HCl in dioxane (10 mL) until the pH was acidic at 0° C. and stirred for 30 min at the same temperature. The reaction mixture was concentrated in vacuo to give a residue that was triturated with ether to give (S)—N-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride as a free flowing solid. Then the compound was dissolved in MeOH, and to the reaction mixture resin was added until the mixture turns basic (Checked by pH paper). The reaction mixture was filtered and the filtrate was concentrated in vacuo to yield the titled intermediate (350 mg, 72%). 1H NMR (400 MHz, DMSO-d6): δ 13.1 (bs, 1H), 8.28 (s, 1H), 8.23 (s, 1H), 4.46 (bs, 2H), 3.36-3.34 (m, 2H), 3.16-3.08 (m, 1H), 2.99-2.86 (m, 2H), 2.50 (bs, 1H), 1.97-1.81 (m, 2H), 1.68-1.58 (m, 2H). LC-MS: m/z [M+1]=219.

Provenance & Evidence