Sodium hydride → 1-(2-aminopyrimidin-4-yl)-1H-indazole-6-carbonitrile

Participants

Reaction Steps

To a solution of 1H-indazole-6-carbonitrile (200 mg, 1.40 mmol) in DMF (2 mL), was added NaH (60% oil dispersion) (89.4 mg, 2.24 mmol). The reaction mixture was stirred for 10 min at RT before addition of 4-chloropyrimidin-2-amine (362 mg, 2.79 mmol). The reaction mixture was stirred at RT for 1 hr then heated at 50° C. in a sealed tube for 18 hr. LC-MS (Method B) indicated a mixture of desired product and a regiosiomer by-product [21%, Retention time=1.65 min, m/z=237.4 (M+H)+] and [29%, Retention time=1.43 min, m/z=237.4 (M+H)+]. The reaction was quenched by addition of water (1 mL) and EtOAc (3 mL). The precipitated solid was collected by suction filtration: LC-MS (Method B): Retention time=1.65 min.

Provenance & Evidence