Water → 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylic acid

HRID 979133Notes

Reaction equation

HRID 979133 reaction equation
[CH3:1][N:2]([C:4]1[CH:22]=[CH:21][C:7]([NH:8][C:9]2[NH:10][C:11](=[O:20])[C:12]([C:15]([O:17]CC)=[O:16])=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:3].[OH-].[Na+].O>C(O)(=O)C>[CH3:3][N:2]([C:4]1[CH:22]=[CH:21][C:7]([NH:8][C:9]2[NH:10][C:11](=[O:20])[C:12]([C:15]([OH:17])=[O:16])=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13562809ethyl 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylate

Product 1

HCID 135628501,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylic acidYield 73.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylate (7.5 g) and sodium hydroxide (3.0 g) are added to water (150 ml), and the mixture is refluxed with stirring for 1 hour. After cooling, the reaction mixture is acidified with acetic acid, and the resulting solid is collected by filtration and recrystallized from DMF. The precipitate is collected by filtration and added to water (50 ml), and the mixture is refluxed with stirring for 1 hour. After cooling, the resulting product is collected by filtration and dried at 80° C. under reduced pressure to give 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylic acid (5 g). M.p. 261°-263° C.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe resulting solid is collected by filtration
  4. customrecrystallized from DMF
  5. filtrationThe precipitate is collected by filtration
  6. additionadded to water (50 ml)
  7. temperaturethe mixture is refluxed
  8. stirringwith stirring for 1 hour
  9. temperatureAfter cooling
  10. filtrationthe resulting product is collected by filtration
  11. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-d1fadec1510643ed9297b5beaaca5b08
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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