A new highly regioselective method for the synthesis of water-soluble 1,3,4-trisubstituted derivatives of tetrahydropyrimidin-2(1H)-one

Submitting author affiliation:
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russian Federation

Beilstein Arch. 2022, 202232. https://doi.org/10.3762/bxiv.2022.32.v1

Published 02 May 2022

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This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.


In this article, we report a regioselective method for the synthesis of new water-soluble 1,3,4-trisubstituted tetrahydropyrimidin-2(1H)-one derivatives containing sodium methanesulfonate fragment in the first position of the heterocycle. The method is based on the reaction of (1-(3,3-diethoxypropyl)ureido)methanesulfonate with aromatic and heterocyclic nucleophiles. The proposed method is distinguished by the possibility of obtaining a wide range of water-soluble substituted tetrahydropyrimidinone derivatives, the absence of the need to use expensive metal complex catalysts, high product yield, and ease of purification.

Keywords: tetrahydropyrimidin-2(1H)-one; electrophilic substitution; C-nucleophiles; acetals

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Smolobochkin, A. V.; Gazizov, A. S.; Yakhshilikova, L. J.; Sidlyaruk, N. A.; Khamatgalimov, A. R.; Burilov, A. R.; Pudovik, M. A. Beilstein Arch. 2022, 202232. doi:10.3762/bxiv.2022.32.v1

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