Oxalic Acid → 2-Oxo-1,2,3,6-Tetrahydropyrimidine-4,6-Dicarboxylic Acid

HRID 2351268Notes

Reaction equation

HRID 2351268 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([C:11]([OH:13])=[O:12])[N:3]=1.C(O)(=O)C(O)=O>C(O)(=O)C.[Zn]>[O:1]=[C:2]1[NH:3][C:4]([C:11]([OH:13])=[O:12])=[CH:5][CH:6]([C:8]([OH:10])=[O:9])[NH:7]1

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 1785245132-Hydroxypyrimidine-4,6-dicarboxylic acid

Product 1

HCID 150520832-Oxo-1,2,3,6-Tetrahydropyrimidine-4,6-Dicarboxylic Acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

2-Hydroxypyrimidine-4,6-dicarboxylic acid (239 mg. 1.30 mmol) was suspended in acetic acid (17M, 60 ml) at 70° with stirring. Zinc dust (600 mg. 9.17 mmol) was added portionwise over a period of 30 min and the mixture was stirred for 1 h at 70° then cooled to room temperature. A solution of oxalic acid (200 mg. 2.22 mmol) in acetic acid (10 ml) was added and the reaction mixture allowed to stand for 5 h. The mixture was filtered and the filtrate evaporated to dryness. The residue was dissolved in hot water (5 ml), filtered and cooled to 4° to 4 days. 2-Oxo-1,2,3,6-tetrahydropyrimidine-4,6-dicarboxylic acid was obtained as off-white crystals (58 mg, 24%).

Workup

  1. stirringthe mixture was stirred for 1 h at 70°
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. dissolutionThe residue was dissolved in hot water (5 ml)
  5. filtrationfiltered
  6. temperaturecooled to 4° to 4 days

Sources & evidence

ORD record
ord-9bcdf2ce32a349ac879c8a1c7a9ffbe1
Source dataset
uspto-grants-1989_10
Patent number
US04873228

Reaction notes

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