Reaction #336835

Reaction equation

sodium bisulfite

sodium hydroxide

hydrochloric acid

sodium hypochlorite

2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid

product

2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid

→

title compound

5-chloro-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidine-carboxylic acid

Solvents

water

Conditions

Workup

1. 1
   Temperaturewith cooling the reaction mixture
2. 2
   Temperaturewith cooling the reaction mixture
3. 3
   Temperaturewas maintained at about 25° C
4. 4
   TemperatureThe mixture was cooled to 10° C.
5. 5
   Otherthe suspended product was isolated by filtration
6. 6
   Washwashed with a minimum amount of cold water
7. 7
   OtherThe product was then dried to constant weight in vacuum-oven at 50° C.

Procedure

To a mixture of 2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (i.e. the product of Step A1 or A2) (9.2 g, 52 mmol) in water (30 mL) and concentrated hydrochloric acid (22 g, 220 mmol) at 15° C. was added dropwise aqueous sodium hypochlorite solution (11%, 40 g, 59 mmol) over 15 minutes so that with cooling the reaction mixture was maintained at 15-20° C. The mixture was then held at 20-25° C. for 1 h. Solid sodium bisulfite (ca. 2 g) was added, and then aqueous sodium hydroxide solution (50%, 8 g, 0.10 mol) was added dropwise so that with cooling the reaction mixture was maintained at about 25° C. The mixture was cooled to 10° C., and the suspended product was isolated by filtration and washed with a minimum amount of cold water. The product was then dried to constant weight in vacuum-oven at 50° C. to afford the title compound (7.5 g).

Source