Reaction #7322

Reaction equation

[(2,4-dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amine

tert-butyl methyl ether

→

phenyl isocyanate

Conditions

Workup

1. 1
   OtherA 500-mL, three-necked flask equipped with a mechanical stirrer

Procedure

A 500-mL, three-necked flask equipped with a mechanical stirrer, thermometer, condenser, and nitrogen-inlet bubbler was charged with [(2,4-dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amine (59.6 g, 209.7 mmol) (from Example 1d supra) and tert-butyl methyl ether (300 mL) (Aldrich). After heating to 55° C. to give a clear solution, phenyl isocyanate (27.48 g, 230.7 mmol) (Aldrich) was added and the mixture was heated to reflux for 10 hours. TLC analysis indicated essentially complete reaction. After cooling to room temperature, the resulting solid was collected by filtration, washed with tert-butyl methyl ether (100 mL), and dried by suction to give N-[(2,4-dichloropyrimidin-5-yl)methyl]-N-(4-methoxyphenyl)(phenylamino) carboxamide as white crystals; 98.46% pure by HPLC analysis. (Yield 78.8 g, 91.3%).

Source