Phenyl chloroformate → HCID 59509064, compound

Participants

Reaction Steps

Phenyl chloroformate (0.15 g, 99 mmol) was added dropwise to a solution of 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (0.20 g, 0.99 mmol) and DIPEA (0.250 g, 1.98 mmol) in dry 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 (3-amino-phenyl)-acetic acid (0.15 g, 0.99 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 combined organic phases were washed with water (2×50 ml) and by brine, dried over anhydrous sodium sulfate and concentrated in a vacuum rotavapor. The residue was washed with ether to give (3-{3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-ureido}-phenyl)-acetic acid as a coloured solid.

Provenance & Evidence