N,N-dimethyl-p-phenylenediamine → ethyl 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylate

HRID 979118Notes

Reaction equation

HRID 979118 reaction equation
CS[C:3]1[NH:4][C:5](=[O:14])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:8]=1.[CH3:15][N:16]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[CH3:17]>C(O)C>[CH3:15][N:16]([C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:3]2[NH:4][C:5](=[O:14])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:8]=2)=[CH:20][CH:19]=1)[CH3:17]

Participants

4

Reactant 2

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 239049Ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylate

Product 1

HCID 13562809ethyl 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylateYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate (20 g) and 4-(N,N-dimethylamino)aniline (19 g) are added to ethanol (200 ml), and the mixture is refluxed with stirring for 19 hours. After cooling, the precipitate is collected by filtration and recrystallized from a mixture of DMF and water to give ethyl 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylate (15.7 g).

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe precipitate is collected by filtration
  4. customrecrystallized from a mixture of DMF and water

Sources & evidence

ORD record
ord-5ed1779484844f8692349d45d4d0f999
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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