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6-Methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazolyl)-pyrimidin-4(1H)-one as CH acid in Michael reaction

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Abstract

Addition of 6-methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one, a compound with two CH-acidic centers, to 5-benzylidenepyrimidine-2,4,6(1H,3H,5H)-trione proceeds with the participation of the atom C5 of pyrimidine ring. Under the realized reaction conditions the latter possesses a greater nucleophilicity as a result of the priority ionization. The obtained Michael adduct is unstable in the neutral aqueous medium and is decomposed into initial oxopyrazolylpyrimidinone, pyrimidine-2,4,6-(1H,3H,5H)-trione, and benzaldehyde.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    A. V. Erkin & V. I. Krutikov

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  1. A. V. Erkin
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  2. V. I. Krutikov
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Correspondence to A. V. Erkin.

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Original Russian Text © A.V. Erkin, V.I. Krutikov, 2009, published in Zhurnal Obshchei Khimii, 2009, vol. 79, no. 7, pp. 1168–1174.

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Erkin, A.V., Krutikov, V.I. 6-Methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazolyl)-pyrimidin-4(1H)-one as CH acid in Michael reaction. Russ J Gen Chem 79, 1525–1531 (2009). https://doi.org/10.1134/S1070363209070214

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  • DOI: https://doi.org/10.1134/S1070363209070214

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