Sodium hydride → 2,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamide

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To a cooled (0° C.) solution of N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine (0.348 g, 1.337 mmol) in anhydrous N,N-dimethylformamide (10 mL) under nitrogen was added sodium hydride (0.064 g, 2.67 mmol, 60% dispersion in mineral oil) in one portion. The reaction mixture was stirred at 0° C. for 15 mins and then a solution of 2,6-dichlorobenzoyl chloride (220 uL, 1.5 mmol) in DMF (1.5 mL) was added dropwise. The mixture was stirred at room temperature for 3.5 hours and then quenched with water (60 mL). The mixture was extracted with ethyl acetate (200 mL). The organic layer was dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (20-80% ethyl acetate/heptane) to give 2,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamide (0.57 g, yield: 100%). LCMS (ESI) m/z: 433.1 [M+H+].

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