Acetic Anhydride → 5-Acetyl-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

HRID 1884546Notes

Reaction equation

HRID 1884546 reaction equation
[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][C:6](=[O:7])[N:5]([CH3:11])[C:3]1=[O:4].[C:12](OC(=O)C)(=[O:14])[CH3:13]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:12]([CH:8]1[C:9](=[O:10])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:11])[C:6]1=[O:7])(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 69860Dimethylbarbituric acid

Product 1

HCID 2746165-Acetyl-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trioneYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 1,3-dimethylbarbituric acid (10 g, 64.04 mmol), 4-dimethylaminopyridine (9.49 g, 158.0 mmol) in dry CH2Cl2 (190 ml) was cooled to 0° C. and acetic anhydride (7.35 ml, 77.9 mmol) added dropwise in 15 min. The reaction mixture was stirred overnight at room temperature, diluted with CH2Cl2 (500 ml) and washed with 2 N HCl solution (80 ml). The organic phase was dried over MgSO4 and evaporated. The residue was crystallised from MeOH, giving 5-acetyl-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 1 (8.6 g, 68%).

Workup

  1. washwashed with 2 N HCl solution (80 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated
  4. customThe residue was crystallised from MeOH

Sources & evidence

ORD record
ord-90c979ec125b4917b3585419ccea6209
Source dataset
uspto-grants-2004_07
Patent number
US06765089B1

Reaction notes

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