Piperidine → HCID 60164413, compound

Participants

Reaction Conditions

Reaction Steps

To a pressure tube was added 2-(6-bromo-1,3-benzodiazol-1-yl)pyrimidin-4-amine (300 mg, 1.03 mmol), piperidine (2 mL), tetrakis(triphenylphosphine)palladium (119.5 mg, 0.10 mmol), copper(I) iodide (19.7 mg, 0.10 mmol) and 2-(1,3-thiazol-2-yl)but-3-yn-2-ol (316.84 mg, 2.07 mmol). The reaction was stirred at 75° C. for 18 h. The reaction mixture was cooled before concentrating in vacuo. The crude product was purified by column chromatography (Biotage) eluted with DCM: methanol gradient (97:3 to 90:1). Material obtained was triturated with methanol to afford the title compound as a beige solid. (43 mg, 11.5% yield); 1H NMR (250 MHz, DMSO) delta 1.91 (3H, s), 6.41 (1H, d, J=5.79 Hz), 7.06 (1H, s), 7.37 (1H, d, J=1.52 Hz), 7.45 (2H, br. s.), 7.65-7.84 (3H, m), 8.19 (1H, d, J=5.79 Hz), 8.62 (1H, d, J=1.07 Hz), 9.00 (1H, s); LC-MS m/z+3.

Provenance & Evidence