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Microwave-assisted N-allylation of uracil and thymine pyrimidine bases

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Chemistry of Heterocyclic Compounds Aims and scope

This work presents a new synthetic approach to N(1)-allylation of pyrimidine nucleobases with allyl bromide. The increased efficiency of the proposed method is based on two specific elements: (a) the nucleoside N-deprotonation is carried out in a homogeneous system by using sodium methylsulfinyl- methylide in DMSO; (b) the allylation reaction is microwave-assisted. This method ensures high yields (87–88%) of the monoallylated products and short reaction time (1.5 h as compared to tens of hours for classical methods), and provides protection against side reactions. NMR analysis of the crude reaction mixture indicated a ratio of 6–8 : 1 between N(1)-allyl derivatives and N(1),N(3)-diallyl derivatives.

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Authors and Affiliations

  1. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania

    L. Sacarescu, I. Atudosie, M. Simionescu, G. Sacarescu & V. Harabagiu

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  1. L. Sacarescu
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  2. I. Atudosie
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  3. M. Simionescu
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  4. G. Sacarescu
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  5. V. Harabagiu
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Correspondence to L. Sacarescu.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 727–731, May, 2011.

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Sacarescu, L., Atudosie, I., Simionescu, M. et al. Microwave-assisted N-allylation of uracil and thymine pyrimidine bases. Chem Heterocycl Comp 47, 602–606 (2011). https://doi.org/10.1007/s10593-011-0804-2

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  • DOI: https://doi.org/10.1007/s10593-011-0804-2

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