2-Chloro-4-methoxypyrimidine → tert-Butyl [3-(4-methoxypyrimidin-2-yl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl (2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate (200 mg, 0.806 mmol, described in Intermediate 4) and sodium bis(trimethylsilyl)amide (1.0 M in THF, 1.69 mL, 1.69 mmol) in THF (0.5 mL) was stirred for 5 min, then 2-chloro-4-methoxypyrimidine (583 mg, 4.03 mmol) was added and argon was bubbled through the mixture for 5 min. The reaction mixture was heated at 130° C. for 10 min in a microwave reactor. The cooled mixture was partitioned between CHCl3 (10 mL) and saturated aqueous NaHCO3 (5 mL). The aqueous phase was extracted further with CHCl3 (10 mL), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane::EtOAc—100:0 to 80:20, to give the title compound. MS: m/z=357 (M+1).

Provenance & Evidence