Sodium hydride → 1-(2-aminopyrimidin-4-yl)-6-bromo-N,N-dimethylindazole-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-N,N-dimethyl-1H-indazole-3-carboxamide (95%, 450 mg, 1.59 mmol) in DMF (10 mL) was added NaH (60% dispension in mineral oil) (60 mg, 1.02 mmol) at 0° C. Mixture was stirred at rt for 10 mins before addition of 4-chloropyrimidin-2-amine (413 mg, 3.19 mmol). The mixture was stirred at 65° C. overnight. The mixture was quenched by addition of water (10 mL). The mixture was extracted with EtOAc (2×15 mL). The combined organics washed with water (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. Trituration with DCM:heptane (4:1) gave the desired product. The filtrate was re-filtered. The solids were combined to give the title compound; 1H NMR (250 MHz, DMSO) delta 3.11 (3H, s), 3.32 (3H, s), 7.08 (1H, d, J=5.48 Hz), 7.19 (1H, d, J=3.35 Hz), 7.58 (1H, dd, J=8.68, 1.68 Hz), 7.95 (1H, d, J=8.53 Hz), 8.34 (1H, d, J=5.63 Hz), 9.18 (1H, d, J=1.22 Hz); LC-MS: m/z=+362.8 (M+H)+.

Provenance & Evidence