Reaction #336846

Reaction equation

Water

sodium hydroxide

6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid

thionyl chloride

ethanol

→

title product

ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate

Conditions

Workup

1. 1
   Temperaturewhile maintaining the temperature below 15° C.
2. 2
   TemperatureThe reaction mixture was then heated
3. 3
   Temperatureat reflux overnight
4. 4
   OtherThe resulting solid was isolated by filtration
5. 5
   Otherdried

Procedure

To a solution of 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid (i.e. the product of Example 4, Step C) (20.0 g, 70.4 mmol) in ethanol (70 mL) was added thionyl chloride (5.14 mL, 70.4 mmol) while maintaining the temperature below 15° C. using an ice bath. The reaction mixture was then heated at reflux overnight. Water was added. Then with external cooling aqueous sodium hydroxide (50%) was added to adjust the pH to 7. The resulting solid was isolated by filtration and dried to afford the title product, a compound of the present invention, as a light beige solid (20.1 g).

Source