Reaction #336841

Reaction equation

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid

D2

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid

thionyl chloride

methanol

ammonia

water

→

title product

methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureat reflux for 24 h
3. 3
   Temperaturethe reaction mixture was heated
4. 4
   Temperatureat reflux for 16 h
5. 5
   TemperatureAfter the mixture was cooled
6. 6
   Otherthe solid was isolated by filtration
7. 7
   Washwashed with water
8. 8
   Otherdried in a vacuum oven at 40° C.

Procedure

To a solution of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (i.e. the product of Step D1 or D2 of Example 2) (2.0 g, 8.5 mmol) in methanol (20 mL) was added dropwise thionyl chloride (4 mL, 70 mmol). The mixture was heated at reflux for 24 h. Concentrated sulfuric acid (5 drops) was added, and the reaction mixture was heated at reflux for 16 h. After the mixture was cooled, water (30 mL) was added, and aqueous ammonia (28%, 10 mL) was added dropwise. The mixture was cooled to 5° C., and the solid was isolated by filtration, washed with water and dried in a vacuum oven at 40° C. to afford the title product (2.3 g), a compound of the present invention.

Source