Ethyl Acetate → 6-(3,4-dimethoxyphenyl)-3-methyl-2,4(1H,3H)-pyrimidinedione

HRID 65146

Reaction equation

HRID 65146 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]([NH2:23])=[O:22].C(OCC)(=O)C>C1C2C(=CC=CC=2)CCC1>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([C:1]2[NH:23][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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11719MethylureaHCID 2758465Ethyl 3,4-dimethoxybenzoylacetate

Product 1

HCID 137142586-(3,4-dimethoxyphenyl)-3-methyl-2,4(1H,3H)-pyrimidinedioneYield 40.3%

Reagents, catalysts & solvents 1

HCID 8404TetralinSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of ethyl veratroylacetate (8.0 g) in tetralin (24 ml) was added N-methylurea (3.52 g) and the mixture was heated for an hour at 170° C. After being cooled to 95° C., ethyl acetate (33 ml) was added thereto. The precipitate was collected by filtration and washed with ethyl acetate to give 6-(3,4-dimethoxyphenyl)-3-methyl-2,4(1H,3H)-pyrimidinedione (3.35 g).

Workup

  1. temperatureAfter being cooled to 95° C.
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ac4b51625d934dca87d4af4f9d803b3c
Source dataset
uspto-grants-1986_09
Patent number
US04612376

Linked notes

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