Phenyl chloroformate → HCID 59508950, compound

Participants

Reaction Steps

To a solution of 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (0.400 g, 1.98 mmol) and DIPEA (0.300 g, 2.38 mmol) in dry dichloromethane (10 ml) was added phenyl chloroformate (0.370 g, 1.98 mmol) dropwise at −78° C. The reaction mixture was then allowed to stir for 16 hours at room temperature. Dichloromethane was evaporated and the residue was dissolved in 1,4-dioxane (15 ml). N,N-dimethylethylenediamine (L) (0.160 g, 1.98 mmol) was added and the mixture was refluxed for 14 hours. The solvent was evaporated and the crude product was re-dissolved in ethyl acetate, washed with water (2×50 ml) and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crude solid product was further purified by silica gel column chromatography (15% methanol/dichloromethane) yielding 1-(2-dimethylamino-ethyl)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-urea. Yield: 293 mg, 47%.

Provenance & Evidence