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Synthesis and Halocyclization of 5-Allyl-2-benzyl(allyl)sulfanyl-6-methylpyrimidin-4(3H)-ones

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Abstract

Alkylation of 5-allyl-6-methyl-2-thiouracil with benzyl chloride and allyl bromide afforded 2-benzyl(allyl)sulfanyl-5-allyl-6-methylpyrimidin-4(3H)-ones. 5-Allyl-2-(benzylsmfanyl)-6-methylpyrirmdin-4(3H)-one reacted with molecular bromine and iodine to give substituted furo[2,3-d]pyrimidines. Depending on the conditions, the reaction of 5-allyl-2-(allylsulfanyl)-6-methylpyrimidin-4(3H)-one with iodine led to the formation of 6-allyl-3-(iodomethyl)-5-methyl-7-oxo-2,3,7,8-tetrahydro[1,3]thiazolo[3,2-a]pyrimidinium iodide or 3,7-bis(iodomethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-d][1,3]thiazolo[3,2-a]pyrimidinium iodide.

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Funding

This study was performed in the framework of state assignment no. 4.9665.2017/8.9.

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Authors and Affiliations

  1. South Ural State University, Chelyabinsk, 454080, Russia

    K. Yu. Petrova, D. G. Kim, V. V. Sharutin & D. M. Zakharova

Authors
  1. K. Yu. Petrova
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  2. D. G. Kim
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  3. V. V. Sharutin
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  4. D. M. Zakharova
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Corresponding author

Correspondence to K. Yu. Petrova.

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The authors declare the absence of conflict of interest.

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Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 1, pp. 41–46.

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Petrova, K.Y., Kim, D.G., Sharutin, V.V. et al. Synthesis and Halocyclization of 5-Allyl-2-benzyl(allyl)sulfanyl-6-methylpyrimidin-4(3H)-ones. Russ J Org Chem 56, 29–33 (2020). https://doi.org/10.1134/S1070428020010054

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  • DOI: https://doi.org/10.1134/S1070428020010054

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