ethyl carbamimidate;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An emulsion of 20.9 g (0.135 mol) of methyl 4-chloroacetoacetate and 23.5 g (0.189 mol) of O-ethylisourea hydrochloride is treated with a solution of 41.3 g (0.31 mol) of sodium hydroxide in 40 ml of water at -20° C. to -10° C. during 5 minutes while stirring well. After stirring at room temperature for 2 hours the resulting crystalline product is filtered off and dried. The crystals, m.p. 156°-158° C., are washed well with diethyl ether. There is obtained 2-ethoxy-4-chloromethyl-6-hydroxy-pyrimidine, m.p. 161°-163° C. After stirring at room temperature for 2 hours the resulting crystalline product is filtered off dried The crystals, m.p. 156°-158° C., are washed well with diethyl ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 24.9 g (0.2 mol) of O-ethylisourea hydrochloride and 21.5 g (0.14 mol) of methyl 4-chloroacetoacetate in 100 ml of methanol is treated at 0°-5° C. during 10 minutes with a solution of 7.55 g (0.33 mol) of sodium in 100 ml of methanol. The mixture is stirred at 0° C. for 2 hours and at room temperature for 18 hours and the solvent is then removed by evaporation under reduced pressure. The residue is dissolved in 300 ml of water and the solution is adjusted to a pH-value of 6. The resulting crystallline product is filtered off, washed with diethyl ether and dried at 40° C. In this manner there is obtained 2-ethoxy-4-chloromethyl-6-hydroxy-pyrimidine, m.p. 157°-159° C. By back-extracting the aqueous filtrate three times with 150 ml of chloroform each time there is obtained an additional amount of this product, m.p. 159°-161° C. the solvent is then removed by evaporation under reduced pressure The residue is dissolved in 300 ml of water The resulting crystallline product is filtered off washed with diethyl ether dried at 40° C