Hydrochloric Acid → 2-(Methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid

HRID 1814760Notes

Reaction equation

HRID 1814760 reaction equation
[CH3:1][S:2][C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([O:12]CC)=[O:11])=[CH:5][N:4]=1.[OH-].[Na+].Cl>O1CCOCC1>[CH3:1][S:2][C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([OH:12])=[O:11])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 239049Ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylate

Product 1

HCID 2958952-(Methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylic acidYield 60.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of ethyl 3,4-dihydro-2-methylthio-4-oxopyrimidine-5-carboxylate (C. W. Todd, J. H. Fletcher and D. S. Tarbell, J. Am. Chem. Soc. (1943), 65, 350-4) (1.95 g) in dioxan (15 ml) was treated with aqueous NaOH (0.73 g in 15 ml) and heated at 85° C. overnight. After cooling, the solution was acidified with 2N HCl to pH3 and the white solid filtered off and dried under vacuum to give title compound (1.03 g). MS (−ve ion chemical ionisation) m/z 185 ([M−H]−, 70%), 141 (100%).

Workup

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

Sources & evidence

ORD record
ord-f52e6cc859224d869869cbb74150d7ba
Source dataset
uspto-grants-2005_04
Patent number
US06878704B2

Reaction notes

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