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

Participants

Reaction Steps

3-Methyl-1-[4-(methyloxy)-2-pyrimidinyl]-2-oxo-4-imidazolidinecarboxylic acid (76 mg, 0.3 mmol) (˜0.3 mmol) in dichloromethane (4 ml) was treated with the 4A molecular sieves (200 mg, 0.300 mmol), and the mixture stirred at RT for 5 minutes. N-Ethylmorpholine (0.190 ml, 1.500 mmol), 1-hydroxybenzotriazole hydrate (55.1 mg, 0.360 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (82 mg, 0.360 mmol) were then added and the reaction stirred at RT under argon for 10 minutes. [(2,4-Dichlorophenyl)methyl]amine (58.1 mg, 0.330 mmol) was added and the reaction left to stir at RT under argon for 4 hours. The reaction mixture was diluted with dichloromethane (15 ml) and saturated sodium hydrogen carbonate solution (20 ml), and the product was extracted into dichloromethane (×2). The combined organic extracts were washed with water (20 ml), brine (20 ml) and then dried over magnesium sulphate. The solvent was evaporated in vacuo to give a yellow solid, which was purified by mass-directed automated HPLC. Fractions containing product were combined and solvent evaporated in vacuo, co-evaporated with diethyl ether to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-[4-(methyloxy)-2-pyrimidinyl]-2-oxo-4-imidazolidinecarboxamide as a white solid (60 mg, 46.3% yield). LC/MS [M+H]+=410, retention time 1.73=minutes.

Provenance & Evidence