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

HRID 621517Notes

Reaction equation

HRID 621517 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.[CH2:19]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])[CH3:20].C(O)C>Cl.O>[CH2:19]([N:21]1[C:1]([C:2]2[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=2)=[CH:13][C:14](=[O:16])[N:24]([CH2:25][CH3:26])[C:22]1=[O:23])[CH3:20]

Participants

6

Reactant 3

HCID 702EthanolHCID 12194sym-DiethylureaHCID 2758465Ethyl 3,4-dimethoxybenzoylacetate

Product 1

HCID 212432281,3-diethyl-6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedioneYield 26.5%

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'-diethylurea (5.06 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 diisopropyl ether and ethyl acetate to give 1,3-diethyl-6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione (3.20 g).

Workup

  1. additionwere added conc
  2. additionTo the residue was added another conc
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with a mixture of diisopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-10247ef6eef2436b8373fa1cfd66fa87
Source dataset
uspto-grants-1989_04
Patent number
US04824851

Reaction notes

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