Reaction #336842

Reaction equation

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

D2

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

thionyl chloride

methanol

→

title product

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

Conditions

Workup

1. 1
   ConcentrationThe mixture was concentrated to 25% of the original volume
2. 2
   workup.ADDITIONdiluted with water (100 mL)
3. 3
   workup.ADDITIONPhenolphthalein pH indicator was added
4. 4
   workup.ADDITION10% aqueous sodium hydroxide was added dropwise
5. 5
   Temperaturewith cooling at 10-20° C.
6. 6
   OtherThe solid was isolated by filtration
7. 7
   Washwashed with water
8. 8
   Otherdried in a vacuum oven at 50-60° 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) (8.5 g, 40 mmol) in methanol (120 mL) was added dropwise with cooling thionyl chloride (15 mL, 200 mmol). The mixture was heated at 60° C. for 24 h. The mixture was concentrated to 25% of the original volume and diluted with water (100 mL). Phenolphthalein pH indicator was added, and 10% aqueous sodium hydroxide was added dropwise with cooling at 10-20° C. to bring the pH to 8-10. The solid was isolated by filtration, washed with water and dried in a vacuum oven at 50-60° C. to afford the title product (7.3 g), a compound of the present invention.

Source