Chemistry of Heterocyclic Compounds

, Volume 42, Issue 6, pp 788–791 | Cite as

Transformations of methyl 6-methyl-2-methylsulfanyl-4-oxo-3,4-dihydro-3-pyrimidinylacetate under oxidative conditions

  • V. Jakubkiene
  • P. Vainilavicius


The oxidation of methyl 6-methyl-2-methylsulfanyl-4-oxo-3,4-dihydro-3-pyrimidinylacetate by reagents which oxidized the SMe group to SO2Me gave the products of the further transformation of the corresponding 2-methylsulfonyl-substituted ester obtained: methyl 5,5-dichloro-6-methoxy-6-methyl-2,4-dioxohexahydro-3-pyrimidinylacetate (using Cl2 in 70 or 50% MeOH), its mixture (about 1:10) with methyl 6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinylacetate (Cl2 in 30% MeOH) or only to the latter compound (Cl2 in H2O, m-ClC6H4CO3H in CHCl3, H2O2 in MeOH). The reaction did not take place with NaOCl in DMF.


methyl 6-methyl-2-methylsulfanyl-4-oxo-3,4-dihydro-3-pyrimidinylacetate methyl 5,5-dichloro-6-methoxy-6-methyl-2,4-dioxohexahydro-3-pyrimidinylacetate methyl 6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinylacetate 


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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • V. Jakubkiene
    • 1
  • P. Vainilavicius
    • 1
  1. 1.Vilnius UniversityVilniusLithuania

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