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

Participants

Reaction Conditions

Reaction Steps

To a pressure tube was added 4-(6-bromo-1H-1,3-benzodiazol-1-yl)pyrimidin-2-amine (70% purity, 790 mg, 1.91 mmol), followed by piperidine (4 mL), tetrakis(triphenylphosphine)palladium (220 mg, 0.19 mmol), copper(I) iodide (36.3 mg, 0.19 mmol)) and 2-(1,3-thiazol-2-yl)but-3-yn-2-ol (584.04 mg, 3.81 mmol). The reaction was capped and stirred at 75° C. for 3.5 hr. The reaction mixture was concentrated in vacuo and purified by flash chromatography (Isolute column, 2% MeOH in DCM to 3% MeOH in DCM) followed by reverse phase preparative HPLC to give the title compound as a pale yellow solid: 1H NMR (500 MHz, DMSO) δ 1.92 (3H, s), 7.03 (1H, br. s.), 7.08-7.20 (3H, m), 7.38 (1H, dd, J=8.35, 1.58 Hz), 7.69 (1H, d, J=3.15 Hz), 7.74 (1H, d, J=8.35 Hz), 7.78 (1H, d, J=3.31 Hz), 8.38 (1H, d, J=5.52 Hz), 8.56 (1H, d, J=0.95 Hz), 9.08 (1H, s); LC-MS: m/z=+363.4 (M+H)+.

Provenance & Evidence