Water → 5-Pyrimidinecarboxylic acid, 1,4-dihydro-2-((2-butoxyphenyl)amino)-4-oxo-

HRID 979125Notes

Reaction equation

HRID 979125 reaction equation
[CH2:1]([O:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[NH:8][C:9]1[NH:10][C:11](=[O:20])[C:12]([C:15]([O:17]CC)=[O:16])=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].O>C(O)(=O)C>[CH2:1]([O:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[NH:8][C:9]1[NH:10][C:11](=[O:20])[C:12]([C:15]([OH:17])=[O:16])=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13562779Ethyl 1,6-dihydro-2-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylate

Product 1

HCID 30627075-Pyrimidinecarboxylic acid, 1,4-dihydro-2-((2-butoxyphenyl)amino)-4-oxo-Yield 72.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 1,6-dihydro-2-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylate (12 g) and sodium hydroxide (3 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 thus obtained is collected by filtration and added to water (100 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-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylic acid (8 g). M.p. 212°-214° C.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe resulting solid is collected by filtration
  4. customrecrystallized from DMF
  5. customThe precipitate thus obtained
  6. filtrationis collected by filtration
  7. additionadded to water (100 ml)
  8. temperaturethe mixture is refluxed
  9. stirringwith stirring for 1 hour
  10. temperatureAfter cooling
  11. filtrationthe resulting product is collected by filtration
  12. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-6db0e4d1950e46a9b872873ecaca64d3
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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