Benzimidazole → HCID 57474742, compound

Participants

Reaction Conditions

Reaction Steps

Methyl-2-(1H-benzo[d]imidazol-1-yl)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. To a solution of 1H-benzo[d]imidazole (0.354 g, 3.0 mmol) in tetrahydrofuran (20 mL) was added sodium hydride (0.120 g, 60% in mineral oil, 30 mmol). The reaction mixture was stirred at 60° C. for 15 min. Methyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (See Example 30.A) (1.014 g, 3 mmol) was added and the resulting solution was stirred for 4 h. The reaction mixture was extracted with EtOAc (3×25 mL) and washed with brine (3×25 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated. The crude material was subjected to silica gel chromatography (25%-40% EtOAc in hexanes). Concentration of the desired fractions afforded the titled compound as yellow solid (1.0 g). MS (ESI) m/z 421.4 [M+1]+.

Provenance & Evidence