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

HRID 1689740Notes

Reaction equation

HRID 1689740 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

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1034422,6-Dihydroxy-5-nitropyrimidine-4-carboxylic acidHCID 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%).

Workup

  1. temperatureThe reaction was refluxed for 12 hrs
  2. filtrationthe white precipitate was collected by filtration
  3. washwashed with water (50 mL×4)
  4. customdried under vacuum for 48 hrs

Sources & evidence

ORD record
ord-a6e21a9b19404e0eb0b261574603f637
Source dataset
uspto-grants-2012_04
Patent number
US08153630B2

Reaction notes

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