Sodium hydride → HCID 67517324, compound

Participants

Reaction Steps

To a solution of 1H-pyrazolo[3,4-d]pyrimidin-4-amine (675 mg, 5 mmol) in DMF (12 mL) was added NaH (60% wt in mineral oil, 240 mg, 6.0 mmol, 1.2 eq) and the mixture was stirred at rt for 0.5 h. The tert-butyl 3-((methylsulfonyl)oxy)piperidine-1-carboxylate (1.67 g, 6 mmol, 1.2 eq) was added and the mixture was heated to 100° C. for 16 h. The solution was cooled to rt and the reaction was quenched with brine (50 mL) and extracted with EtOAc (80 mL×4). The organic layers were dried over Na2SO4, concentrated in vacuo to afford a residue which was purified by column chromatography (silica gel, pure EtOAc) to give the title product (700 mg, yield: 50%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.24 (br s, 1H), 8.72 (br s, 1H), 8.41 (s, 1H), 8.33 (s, 1H), 4.67-4.62 (m, 1H), 4.05-3.58 (m, 3H), 3.40-3.33 (m, 1H), 2.98-2.95 (m 1H), 2.16-2.04 (m, 1H), 1.61-1.24 (m, 11H). ESI-MS (M+H+): 319.0.

Provenance & Evidence