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

HRID 979124Notes

Reaction equation

HRID 979124 reaction equation
[CH2:1]([O:4][C:5]1[CH:23]=[CH:22][CH:21]=[CH:20][C:6]=1[NH:7][C:8]1[NH:9][C:10](=[O:19])[C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=1)[CH2:2][CH3:3].[OH-].[Na+].O>C(O)(=O)C>[CH2:1]([O:4][C:5]1[CH:23]=[CH:22][CH:21]=[CH:20][C:6]=1[NH:7][C:8]1[NH:9][C:10](=[O:19])[C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13562777Ethyl 1,6-dihydro-2-(2-propoxyanilino)-6-oxo-5-pyrimidinecarboxylate

Product 1

HCID 30627065-Pyrimidinecarboxylic acid, 1,4-dihydro-4-oxo-2-((2-propoxy)phenyl)amino)-Yield 61.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 1,6-dihydro-2-(2-propoxyanilino)-6-oxo-5-pyrimidinecarboxylate (8 g) and sodium hydroxide (3 g) are added to water (100 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 (100 ml), and the mixture is refluxed with stirring for 1 hour. After cooling, the product is collected by filtration and dried at 80° C. under reduced pressure to give 1,6-dihydro-2-(2-propoxyanilino)-6-oxo-5-pyrimidinecarboxylic acid (4.5 g). M.p. 202°-204° 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 (100 ml)
  7. temperaturethe mixture is refluxed
  8. stirringwith stirring for 1 hour
  9. temperatureAfter cooling
  10. filtrationthe product is collected by filtration
  11. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-f93f74fd79c249b188601723f8c72b6a
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

Loading…