Methanol → Methyl 5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

Reaction equation

[K].[N+:2]([C:5]1[C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:6]=1[C:7]([OH:9])=[O:8])([O-:4])=[O:3].OS(O)(=O)=O.[CH3:21]O>>[N+:2]([C:5]1[C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:6]=1[C:7]([O:9][CH3:21])=[O:8])([O-:4])=[O:3]

Participants

Reactant 4

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 1034421,2,3,6-Tetrahydro-5-nitro-2,6-dioxo-4-pyrimidinecarboxylic acid

HCID 5462222Potassium

Product 1

HCID 238725Methyl 5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

Procedure

The potassium salt of 5-nitroorotic acid (25.0 g, 0.1 mol) was dissolved in MeOH (75 ml). Concentrated H2SO4 (21 mL) was added drop wise. The reaction was refluxed for 12 hrs. After cooling to room temperature, the white precipitate was collected by filtration, washed with water (50 mL×4), and dried under vacuum for 48 hrs. to afford compound 2 as a white power (26.0 g, 75%).