2,4-Dichlorobenzylamine → N-[(2,4-dichlorophenyl)methyl]-1-(5-fluoro-2-pyrimidinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide

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Reaction Steps

1-(5-Fluoro-2-pyrimidinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid (211 mg, 0.878 mmol) was suspended in dichloromethane (5 ml) under argon and treated with N-ethylmorpholine (0.667 ml, 5.27 mmol), 1-hydroxybenzotriazole hydrate (161 mg, 1.054 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (202 mg, 1.054 mmol) and stirred at room temperature for ˜5 minutes. The mixture was then treated with 1-(2,4-dichlorophenyl)methanamine (0.117 ml, 0.878 mmol) and left to stir overnight at room temperature. The mixture was diluted with dichloromethane (˜10 ml) and washed with saturated sodium hydrogen carbonate solution, water, 10% aqueous citric acid, water, and brine, then filtered through a hydrophobic frit and evaporated. Trituration of the resulting oil with diethyl ether gave N-[(2,4-dichlorophenyl)methyl]-1-(5-fluoro-2-pyrimidinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide (187 mg, 53.5% yield) as a white solid which was collected by filtration and dried in vacuo. LC/MS [M+H]+=398, retention time=2.12 minutes.

Provenance & Evidence