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

HRID 65144Notes

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

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

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

Sources & evidence

ORD record: ord-b65695f6e6364535a1c7a07535782a91
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04612376

Reaction notes

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