Reaction #56843

Reaction equation

guanidine hydrochloride

diethyl methylmalonate

sodium methoxide

→

2-amino-4,6-dihydroxy-5-methyl-pyrimidine

Yield 90.0%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherAfter evaporation of volatiles under reduced pressure
2. 2
   workup.ADDITIONthe residue was treated with 1.0 M hydrochloric acid until pH=2
3. 3
   FiltrationFiltration
4. 4
   Otherdrying

Procedure

To a stirred mixture of guanidine hydrochloride (1.91 g, 20.0 mmol) and diethyl methylmalonate (3.48 g, 20.0 mmol) in ethanol (30 ml) was added sodium methoxide (2.7 g, 50.0 mmol, 25% in methanol) dropwise. The cloudy mixture was stirred at 60-70° C. for 16 hours. After evaporation of volatiles under reduced pressure, the residue was treated with 1.0 M hydrochloric acid until pH=2. Filtration and drying provided 2-amino-4,6-dihydroxy-5-methyl-pyrimidine (2.5 g, 90% yield) as a white powder.

Source