Acetamidine monohydrochloride → Ethyl 2,4-dimethylpyrimidine-5-carboxylate
Reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].[O-]CC.[Na+].C(O)C.[C:13]([C:16](=[CH:22]N(C)C)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=O)[CH3:14]>>[CH3:3][C:2]1[N:5]=[C:13]([CH3:14])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][N:4]=1Participants
4
Procedure
Acetamidine hydrochloride was added to a 10% sodium ethoxide-ethanol solution (410 mL, 0.53 mol) at room temperature. Then, ethyl 2-acetyl-3-(dimethylamino)acrylate (98 g, 0.53 mol) was added to the mixture, and the mixture was heated under reflux for 24 hrs. Ethanol was evaporated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was evaporated. The residue was distilled under reduced pressure to give the title compound (73 g, yield 76%).