Malonic Acid → 1-Methyl-2,4,6(1H,3H,5H)-pyrimidinetrione

HRID 2389515Notes

Reaction equation

HRID 2389515 reaction equation
[C:1]([OH:7])(=O)[CH2:2][C:3]([OH:5])=O.[CH3:8][NH:9][C:10]([NH2:12])=[O:11].C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:8][N:9]1[C:1](=[O:7])[CH2:2][C:3](=[O:5])[NH:12][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 7918Acetic AnhydrideHCID 11719Methylurea

Product 1

HCID 757221-Methyl-2,4,6(1H,3H,5H)-pyrimidinetrioneYield 65.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70° C., acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90° C. for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8%). m.p.=131.2-133.1° C. [Lit.1: m.p.=130-131.5° C.].

Workup

  1. additionAfter the completion of the addition
  2. temperaturecooled to room temperature
  3. customThe solvent is removed under reduced pressure
  4. additionthe residue is treated with 350 mL of ethanol
  5. customto precipitate out yellowish solid
  6. customThe solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-16013d51fe7d4ea4a737323dc0b8fefa
Source dataset
uspto-grants-2012_09
Patent number
US08273750B2

Reaction notes

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