Sodium hydride → 4-{6-bromo-3-[(dimethylamino)methyl]-1H-indazol-1-yl}pyrimidin-2-amine

Participants

Reaction Steps

To a solution of (6-Bromo-1H-indazol-3-ylmethyl)-dimethyl-amine (523 mg, 2.05 mmol) in DMF (8 mL) was added NaH (60% oil dispersion) (132 mg, 3.29 mmol) at 0° C. The reaction mixture was allowed to warm up to RT and was stirred for 15 min. A solution of 4-chloropyrimidin-2-amine (533 mg, 4.11 mmol) in DMF (3 mL) was added slowly. The resulting mixture was stirred at 60° C. for 18 hr. When the reaction mixture was partitioned between EtOAc (25 mL) and water (10 mL), precipitation occurred. The solid was collected by suction filtration and was washed with EtOAc to give the title compound: 1H NMR (500 MHz, DMSO) δ 2.22 (6H, s), 3.81 (2H, s), 7.04 (1H, d, J=5.52 Hz), 7.06-7.19 (2H, m), 7.50 (1H, m, J=8.51 Hz), 7.92 (1H, d, J=8.51 Hz), 8.27 (1H, d, J=5.52 Hz), 9.11 (1H, d, J=1.26 Hz); LC-MS: m/z=+348.9 (M+H)+.

Provenance & Evidence