Phenyl chloroformate → HCID 59509129, compound

Participants

Reaction Steps

Phenyl chloroformate (0.370 g, 1.98 mmol) was added dropwise to a solution of 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (0.25 g, 1.2 mmol) and DIPEA (0.31 g, 2.4 mmol) in dichloromethane (10 ml) at −78° C. and the mixture was allowed to stir overnight at room temperature. Then dichloromethane was evaporated, dry 1,4-dioxane and glycine ethyl ester hydrochloride (0.17 g, 1.2 mmol) and DIPEA (0.31 g, 2.4 mmol) were added and the mixture was heated overnight at 70° C. The solvent was evaporated and the crude product was extracted with ethyl acetate (2×100 ml). The ethyl acetate phase was washed with water (2×50 ml) and brine, dried over anhydrous sodium sulfate and concentrated in a vacuum rotavapor. The residue was purified by silica gel column chromatography (eluent: 70% ethyl acetate/hexane) giving {3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-ureido}-acetic acid ethyl ester. Yield: 190 mg, 47.8%.

Provenance & Evidence