2-Methyl-3-butyn-2-ol → [1-(2-aminopyrimidin-4-yl)-3-[(dimethylamino)methyl]-1H-indazol-6-yl]-2-methylbut-3-yn-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{6-bromo-3-[(dimethylamino)methyl]-1H-indazol-1-yl}pyrimidin-2-amine (80 mg, 0.23 mmol) in piperidine (2 mL) was added 2-methyl-but-3-yn-2-ol (38.8 mg, 0.461 mmol), CuI (4.4 mg, 0.023 mmol) and tetrakis(triphenylphosphine)palladium (13.3 mg, 0.012 mmol). The mixture was heated at 75° C. for 1 hr in a sealed tube. Volatiles were removed by concentration in vacuo. Purification by flash chromatography (Isolute column, 100% DCM to 5% MeOH in DCM) afforded the title compound as yellow solid: 1H NMR (500 MHz, DMSO) δ 1.53 (6H, s), 2.23 (6H, s), 3.80 (2H, s), 5.51 (1H, s), 6.93-7.09 (2H, m), 6.97-7.04 (1H, m), 7.32 (1H, d, J=8.20 Hz), 7.93 (1H, s), 8.19-8.35 (1H, m), 8.84 (1H, s); LC-MS: m/z=+351.10 (M+H)+.

Provenance & Evidence