Ethanol → 6-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

HRID 621516Notes

Reaction equation

HRID 621516 reaction equation
[C:1]([CH2:13][C:14]([O:16]CC)=O)(=O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[CH3:19][NH:20][C:21]([NH:23][CH3:24])=[O:22].C(O)C>Cl.O>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([C:1]2[N:23]([CH3:24])[C:21](=[O:22])[N:20]([CH3:19])[C:14](=[O:16])[CH:13]=2)[CH:11]=[CH:10][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 702EthanolHCID 7293N,N'-DimethylureaHCID 2758465Ethyl 3,4-dimethoxybenzoylacetate

Product 1

HCID 140964656-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedioneYield 69.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalyst2×HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of ethyl veratroylacetate (10 g) and N,N'-dimethylurea (3.84 g) were added conc. hydrochloric acid (1 drop) and ethanol (1 ml). The mixture was heated at 120° C. for 3.5 hours under reduced pressure. To the residue was added another conc. hydrochloric acid (2 drops) and the mixture was heated again at 120° C. for 4 hours under reduced pressure. To the reaction mixture was added water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with a mixture of isopropyl ether and ethyl acetate to give 6-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione (7.60 g).

Workup

  1. temperaturethe mixture was heated again at 120° C. for 4 hours under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with a mixture of isopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-05fdc1e23fdf451495d7dc3c2b9a7952
Source dataset
uspto-grants-1989_04
Patent number
US04824851

Reaction notes

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