Reaction #336845

Reaction equation

N-chlorosuccinimide

water

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

product

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

N-chlorosuccinimide

→

title product

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

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   TemperatureThen the reaction mixture was heated at 55° C. for 3 h
2. 2
   Temperaturethe reaction mixture was maintained at 55° C. for 30 minutes
3. 3
   workup.ADDITIONwas added
4. 4
   OtherThe resulting solid was isolated by filtration
5. 5
   Washwashed with water
6. 6
   workup.DISSOLUTIONdissolved in ethyl acetate
7. 7
   Washwashed with water
8. 8
   Otherdried
9. 9
   OtherThe solvent was removed
10. 10
    Othera rotary evaporator

Procedure

To a solution of 6-amino-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid (i.e. the product of Step B) (75 g, 300 mmol) in N,N-dimethylformamide (300 mL) at 50° C. was added portionwise N-chlorosuccinimide (44.1 g, 330 mmol). The temperature of the reaction mixture increased exothermically to 65° C. Then the reaction mixture was heated at 55° C. for 3 h. Additional N-chlorosuccinimide (14 g, 90 mmol) was added portionwise, and the reaction mixture was maintained at 55° C. for 30 minutes. After the reaction mixture was cooled water was added. The resulting solid was isolated by filtration, washed with water, dissolved in ethyl acetate, washed with water and dried. The solvent was removed using a rotary evaporator to afford the title product, a compound of the present invention, as a tan solid (73.68 g).

Source