DIMETHYL 2-OXOSUCCINATE

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-Amino-2-fluorotoluene (4.89 g, 39.1 mmol), dimethyl 2-oxobutanedioate (6.26 g, 39.1 mmol), and TosicAcid (0.223 g, 1.172 mmol) were heated at reflux under Dean-Stark conditions for 1 hour. The solvent was removed in vacuo and the residue purified by column chromatography on a silica gel column, eluting with EtOAc/hexane (0-15%) to afford Dimethyl(2E)-2-[(2-fluoro-3-methylphenyl)imino]butanedioate (7-6, 5.48 g, 53% yield) as a clear oil, LCMS shows the compound is 100% pure, LRMS m/z (M+H)+ 268.2 found, 268.1 required. at reflux under Dean-Stark conditions for 1 hour The solvent was removed in vacuo the residue purified by column chromatography on a silica gel column eluting with EtOAc/hexane (0-15%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-Amino-5-methyl-1H-s-triazole (112 mg) and 320 mg of dimethyl 2-oxo-succinate are dissolved in 5 ml of glacial acetic acid. After boiling under reflux for 22 hours the solvent is distilled off in a vacuum. The residue is suspended in warm methanol. After cooling the product is filtered off and washed several times with methanol. After drying in a high vacuum there are obtained 73 mg of methyl 7-hydroxy-2-methyl-s-triazolo[1,5-a]pyrimidine-5-carboxylate as a beige powder, m.p.>220° C. under reflux for 22 hours the solvent is distilled off in a vacuum After cooling the product is filtered off washed several times with methanol After drying in a high vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-Amino-5-methyl-1H-s-triazole (112 mg) and 320 mg of dimethyl 2-oxo-succinate are dissolved in 5 ml of glacial acetic acid. After boiling under reflux for 22 hours the solvent is distilled off in a vacuum. The residue is suspended in warm methanol. After cooling the product is filtered off and washed several times with methanol. After drying in a high vacuum there are obtained 73 mg of methyl 7-hydroxy-2-methyl-s-triazolo[1,5-a]pyrimidine-5-carboxylate as a beige powder, m.p.>220° C. under reflux for 22 hours the solvent is distilled off in a vacuum After cooling the product is filtered off washed several times with methanol After drying in a high vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-Amino-2-fluorotoluene (4.89 g, 39.1 mmol), dimethyl 2-oxobutanedioate (6.26 g, 39.1 mmol), and TosicAcid (0.223 g, 1.172 mmol) were heated at reflux under Dean-Stark conditions for 1 hour. The solvent was removed in vacuo and the residue purified by column chromatography on a silica gel column, eluting with EtOAc/hexane (0-15%) to afford Dimethyl(2E)-2-[(2-fluoro-3-methylphenyl)imino]butanedioate (7-6, 5.48 g, 53% yield) as a clear oil, LCMS shows the compound is 100% pure, LRMS m/z (M+H)+ 268.2 found, 268.1 required. at reflux under Dean-Stark conditions for 1 hour The solvent was removed in vacuo the residue purified by column chromatography on a silica gel column eluting with EtOAc/hexane (0-15%)