Reaction #336844

Reaction equation

acetonitrile

phosphorus oxychloride

2-(4-chlorophenyl)-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid

product

2-(4-chlorophenyl)-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid

→

title compound

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

Solvents

water

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature the reaction mixture
2. 2
   Otherthe temperature between 35 and 45° C
3. 3
   Otherwas isolated by filtration
4. 4
   Washwashed with water
5. 5
   Temperatureheated to 80° C. for 18 h
6. 6
   OtherAfter 2 days at room temperature the solid was isolated by filtration
7. 7
   Washwashed with water
8. 8
   OtherA second crop was obtained
9. 9
   Temperatureby cooling the filtrate and refiltering
10. 10
    OtherThe combined solids were dried

Procedure

To phosphorus oxychloride (180 mL) was added 2-(4-chlorophenyl)-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (i.e. the product of Step A) (81.81 g, 326 mmol). The mixture was heated to 90° C. for 2.5 h. After cooling to room temperature the reaction mixture was slowly added to 1:2 acetonitrile:water (1.5 L) while keeping the temperature between 35 and 45° C. After the reaction mixture was stirred at room temperature for 30 minutes the resulting solid was isolated by filtration and washed with water. The solid was then combined with aqueous ammonia (5%, 2.1 L) and heated to 80° C. for 18 h. After 2 days at room temperature the solid was isolated by filtration and washed with water. A second crop was obtained by cooling the filtrate and refiltering. The combined solids were dried to afford the title compound (58.8 g).

Source