Sodium hydride → 2,6-dichloro-N-(6-chloro-5-fluoropyrimidin-4-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-5-fluoropyrimidin-4-amine (1.21 g, 8.2 mmol) in DMF (25 mL) at 0° C. was added NaH (60% in mineral oil, 0.46 g, 11.5 mmol). The reaction mixture was stirred at 0° C. for 20 minutes. 2,6-dichlorobenzoyl chloride (2.06 g, 9.8 mmol) was then added dropwise over 5 minutes. The reaction mixture was warmed to room temperature and stirred under nitrogen overnight. The reaction was quenched with saturated NH4Cl solution (100 mL), and extracted with EtOAc (3×100 mL). The combined organics layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with 0-25% EtOAc in hexane gradient to give the desired compound as a white solid (1.32 g, 50% yield). 1H NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 8.10 (s, 1H), 7.39-7.35 (m, 3H). LCMS (ESI) m/z: 320.0 [M+H+].

Provenance & Evidence