Piperidine → 4-[1-(2-aminopyrimidin-4-yl)-2-(2-methoxyethoxy)-1H-1,3-benzodiazol-6-yl]-2-(pyrimidin-2-yl)but-3-yn-2-ol

関与物質

反応手順

To a pressure tube was added 4-[6-iodo-2-(2-methoxyethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (70%, 120 mg, 0.2 mmol) followed by piperidine (1.0 mL), tetrakis(triphenylphosphine)palladium(0) (23.61 mg, 0.02 mmol), copper(I) iodide (3.89 mg, 0.02 mmol) and 2-(pyrimidin-2-yl)but-3-yn-2-ol (60.53 mg, 0.41 mmol). The reaction was capped and stirred at RT for 1 h. The reaction mixture was concentrated in vacuo. The crude material was purified by flash column chromatography (1-10% MeOH gradient in DCM), followed by trituration with EtOAc/heptanes/DCM to give the title compound: 1H NMR (500 MHz, DMSO) delta 1.88 (3H, s), 3.92-3.64 (2H, m), 4.84-4.59 (2H, m), 6.13 (1H, s), 6.97 (1H, d, J=5.5 Hz), 7.10 (2H, s), 7.23 (1H, dd, J=8.2, 1.5 Hz), 7.44 (1H, d, J=8.1 Hz), 7.49 (1H, t, J=4.8 Hz), 8.13 (1H, s), 8.39 (1H, d, J=5.5 Hz), 8.89 (2H, d, J=4.9 Hz); LC-MS: m/z=+432.05 (M+H)+.

情報源と証拠