Hydrochloric Acid → 4-Oxo-1,4-dihydropyrimidine-5-carboxylic acid

HRID 1814759Notes

Reaction equation

HRID 1814759 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[CH:4][NH:3]1.Cl>[OH-].[Na+]>[O:1]=[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][NH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 963476-Oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 151367864-Oxo-1,4-dihydropyrimidine-5-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3,4-dihydro-4-oxopyrimidine-5-carboxylate (K R Huffman, F C Schaefer and G A Peters, J. Org. Chem. (1962) 27, 551-8) (1.68 g) was dissolved in 1N NaOH (23 ml) and heated at 60° C. overnight. After cooling in ice, the solution was acidified to pH2 with 2N HCl, stirred 5 mins and the solid filtered off and dried under vacuum to give title compound (1.25 g).

Workup

  1. temperatureAfter cooling in ice
  2. filtrationthe solid filtered off
  3. customdried under vacuum

Sources & evidence

ORD record
ord-251c13cbe65e4f728a9cc85843493766
Source dataset
uspto-grants-2005_04
Patent number
US06878704B2

Reaction notes

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