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Synthesis of pyrido[2,3-d]pyrimidines from 6-amino-1,3-dimethyluracil and aldehydes

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Abstract

6-Amino-1,3-dimethyluracil reacted with aliphatic aldehydes on heating in formic acid to give mixtures of 1,3,7,9-tetramethylpyrido[2,3-d: 6,5-d']dipyrimidine-2,4,6,8(1H,3H,7H,9H)-tetraone and the corresponding 5,6-dialkyl-1,3-dimethylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-diones. The reaction of 6-amino-1,3-dimethyluracil with 3-phenylprop-2-enal under analogous conditions afforded 6-benzyl-1,3-dimethyl-5-[(E)-2-phenylvinyl]pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione and 1,3-dimethyl-5-phenylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione. 1,3-Dimethyl-7-phenylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione was obtained in the reaction of the title compound with 3-phenylpropynaldehyde diethyl acetal.

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Authors and Affiliations

  1. Ural Federal University, ul. Mira 19, Yekaterinburg, 620002, Russia

    Yu. A. Azev, O. S. Ermakova, A. M. Gibor & V. A. Bakulev

  2. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990, Russia

    M. A. Ezhikova & M. I. Kodess

Authors
  1. Yu. A. Azev
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  2. O. S. Ermakova
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  3. A. M. Gibor
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  4. V. A. Bakulev
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  5. M. A. Ezhikova
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  6. M. I. Kodess
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Correspondence to Yu. A. Azev.

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Original Russian Text © Yu.A. Azev, O.S. Ermakova, A.M. Gibor, V.A. Bakulev, M.A. Ezhikova, M.I. Kodess, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 12, pp. 1817–1820.

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Azev, Y.A., Ermakova, O.S., Gibor, A.M. et al. Synthesis of pyrido[2,3-d]pyrimidines from 6-amino-1,3-dimethyluracil and aldehydes. Russ J Org Chem 51, 1784–1787 (2015). https://doi.org/10.1134/S1070428015120210

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  • DOI: https://doi.org/10.1134/S1070428015120210

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