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The Silyl Method for the Synthesis of 1[-2(Phenoxy)ethyl]uracils

Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A modification of the method for the synthesis of N(1)-substituted derivatives of uracil is proposed using the Gilbert-Johnson reaction, which consists of the alkylation of 5-substituted 2,4-bis(trimethylsiloxy)pyrimidines with 1-bromo-2-(phenoxy)ethanes of low reactivity at 180-185° without solvent. The corresponding 1-[2-(phenoxy)ethyl]uracils, which were obtained in 55-74% yield, contained no impurities of the N(1), N(3)-disubstituted compounds.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, 1071–1075, July, 2005.

cf E. Ya. Lukevics and A. E. Zablotskaya. The Silyl Method for the Synthesis of Nucleosides [in Russian], Zinatne, Riga, 1985, 440 p. (Editor's note).

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Novikov, M.S., Ozerov, A.A. The Silyl Method for the Synthesis of 1[-2(Phenoxy)ethyl]uracils. Chem Heterocycl Compd 41, 905–908 (2005). https://doi.org/10.1007/s10593-005-0246-9

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  • DOI: https://doi.org/10.1007/s10593-005-0246-9

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