Water → HCID 13562822, compound

HRID 979127Notes

Reaction equation

HRID 979127 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=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.[OH-].[Na+].O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=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

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13562781HCID 13562781, compound

Product 1

HCID 13562822HCID 13562822, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 1,6-dihydro-2-(3-methoxyanilino)-6-oxo-5-pyrimidinecarboxylate (3 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 is collected by filtration and added to water (60 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-(3-methoxyanilino)-6-oxo-5-pyrimidinecarboxylic acid (1.8 g). M.p. 247°-249° 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 (60 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-9a7f9deefa9345f4aa084f2d2401bf40
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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