Reaction #1064136

Reaction equation

p-toluenesulfonic acid monohydrate

bromine

sodium acetate

2,4-diamino-6-hydroxypyrimidine

→

p-toluenesulfonate

Solvents

Ethanol

acetonitrile

water

acetonitrile

Conditions

Workup

1. 1
   Temperaturecooled
2. 2
   Concentrationconcentrated under vacuum
3. 3
   OtherThe resulting residue is triturated (2×5 ml of water)
4. 4
   Otherdecanted
5. 5
   TemperatureAfter heating
6. 6
   Temperatureunder reflux for 20 minutes the mixture
7. 7
   Temperatureis cooled to room temperature
8. 8
   Filtrationfiltered
9. 9
   WashThe precipitate is washed with ethanol (2×5ml)
10. 10
    Otherdried

Procedure

To 300 mg (0.766 mmol) of N-4-(1-methoxy-1-buten-4-yl)benzoyl-L-glutamic acid diethyl ester, 3.0 ml of acetonitrile, and 3.0 ml of water, stirred at room temperature, are added 122 mg (0.766 mmol) of bromine in 1 ml of acetonitrile. To this solution is added 188 mg (2.3 mmol) of sodium acetate and 0.97 mg (0.77 mmol) of 2,4-diamino-6-hydroxypyrimidine and the resulting mixture is heated to 60° C. for 18 hours, cooled, then concentrated under vacuum. The resulting residue is triturated (2×5 ml of water) and decanted. Ethanol (5 ml) and 440 mg (2.3 mmol) of p-toluenesulfonic acid monohydrate are added. After heating under reflux for 20 minutes the mixture is cooled to room temperature and filtered. The precipitate is washed with ethanol (2×5ml) and dried to obtain a p-toluenesulfonate salt of the title compound.

Source