C([O-])C.[Na+].Cl.[C:6]([NH2:9])(=[NH:8])[CH3:7].[CH2:10]([O:12][C:13](=[O:28])[C:14]([C:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Br:26])=[CH:15]N(C)C)[CH3:11]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Br:26])=[N:8][C:6]([CH3:7])=[N:9][CH:15]=1)=[O:28])[CH3:11]To a fresh prepared solution of sodiumethanolate (prepared from 0.77 g (33.7 mmol) Na in 100 ml Ethanol) 3.18 g (33.7 mmol) acetamidinhydrochloride was added. After 10 Min. a solution of 10.0 g (30.6 mmol) 2-(2-bromo-benzoyl)-3-dimethylamino-acrylic acid ethyl ester in 120 ml ethanol was added and the reaction mixture heated for 16 hrs. at 80°. The solvent was evaporated, the residue distributed between 100 ml H2O and 100 ml CH2Cl2. The aqueous phase was extracted twice with 100 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtrated and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 40:1) to give 8.3 g (84%) 4-(2-bromo-phenyl)-2-methyl-pyrimidine-5-carboxylic acid ethyl ester as a pale brown oil.
Loading…
