Methylmalonic Acid → 1,3,5-Trimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione

HRID 463294

Reaction equation

HRID 463294 reaction equation
[CH3:1][NH:2][C:3]([NH:5][CH3:6])=[O:4].[CH3:7][CH:8]([C:12]([OH:14])=O)[C:9]([OH:11])=O.C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:1][N:2]1[C:9](=[O:11])[CH:8]([CH3:7])[C:12](=[O:14])[N:5]([CH3:6])[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 487Methylmalonic AcidHCID 7293N,N'-DimethylureaHCID 7918Acetic Anhydride

Product 1

HCID 818201,3,5-Trimethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneYield 42%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

75 g (0.85 mol) of 1,3-dimethylurea and 102 g (0.86 mol) of methyl malonic acid were dissolved in 300 ml of glacial acetic acid at 65° C. To the solution was added 330 ml of acetic anhydride, the temperature was gradually raised and the mixture was refluxed by heating at 90° C. for 6 hours. The reaction solution was concentrated under reduced pressure, and benzene was added to the residue. The crystals thus-deposited were collected by filtration and recrystallized from benzene to obtain 60 g of 1,3,5-trimethylbarbituric acid. Yield: 42%, Melting Point: 83° to 85° C.

Workup

  1. temperaturethe temperature was gradually raised
  2. temperaturethe mixture was refluxed
  3. concentrationThe reaction solution was concentrated under reduced pressure, and benzene
  4. additionwas added to the residue
  5. filtrationThe crystals thus-deposited were collected by filtration
  6. customrecrystallized from benzene

Sources & evidence

ORD record
ord-f269a157919840d7a4b8c7fd091a9142
Source dataset
uspto-grants-1985_05
Patent number
US04518685

Linked notes

Loading…