Acetic Acid → 5-Pyrimidinecarboxylic acid, 1,4-dihydro-2-((2-ethoxyphenyl)amino)-4-oxo-

HRID 979123Notes

Reaction equation

HRID 979123 reaction equation
[CH2:1]([O:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[NH:6][C:7]1[NH:8][C:9](=[O:18])[C:10]([C:13]([O:15]CC)=[O:14])=[CH:11][N:12]=1)[CH3:2].[OH-].[Na+].C(O)(=O)C>O>[CH2:1]([O:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[NH:6][C:7]1[NH:8][C:9](=[O:18])[C:10]([C:13]([OH:15])=[O:14])=[CH:11][N:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 13562776Ethyl 1,6-dihydro-2-(2-ethoxyanilino)-6-oxo-5-pyrimidinecarboxylate

Product 1

HCID 30627055-Pyrimidinecarboxylic acid, 1,4-dihydro-2-((2-ethoxyphenyl)amino)-4-oxo-Yield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethyl 1,6-dihydro-2-(2-ethoxyanilino)-6-oxo-5-pyrimidinecarboxylate (3.4 g) and sodium hydroxide (1 g) are added to water (50 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 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-(2-ethoxyanilino)-6-oxo-5-pyrimidinecarboxylic acid (2 g). M.p. 226°-228° 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. temperaturethe mixture is refluxed
  7. stirringwith stirring for 1 hour
  8. temperatureAfter cooling
  9. filtrationthe resulting product is collected by filtration
  10. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-1b19a7d30bda4e11b605edaabfb2ee02
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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