Piperidine → HCID 60164410, compound

Participants

Reaction Conditions

Reaction Steps

To a pressure tube was added 3-(2-aminopyrimidin-4-yl)-7-bromo-6-fluoro-1,3benzodiazol-4-amine (66%, 250 mg, 0.54 mmol), piperidine (1.5 mL), tetrakis(triphenylphosphine)palladium (61.9 mg, 0.05 mmol), copper(I) iodide (10.2 mg, 0.05 mmol) and 2-methylbut-3-yn-2-ol (0.1 ml, 1.07 mmol). The reaction was stirred at 75° C. for 2.5 h before concentrating in vacuo. The crude product was purified by column chromatography (Biotage) eluted with DCM: methanol gradient (98:3 to 90:10). Material obtained triturated with methanol to obtain the title compound as an off-white solid. (45 mg, 26.7% yield); 1H NMR (500 MHz, DMSO) delta 1.52 (6H, s), 5.53 (1H, s), 7.14 (1H, d, J=5.20 Hz), 7.18 (2H, br. s.), 7.67 (1H, d, J=9.62 Hz), 8.40 (1H, br. s.), 8.63 (1H, d, J=6.62 Hz), 9.16 (1H, s); LC-MS m/z+312.5 (M+H)+.

Provenance & Evidence