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Synthesis of trichloromethylpyrimidines and trichloromethylpyrimido [4,5-d]pyrimidines from alkyl 2-(diaminomethylidene)-3-oxobutyrates and trichloroacetonitrile

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Russian Chemical Bulletin Aims and scope

Heterocyclization of alkyl 2-(diaminomethylidene)-3-oxobutyrates with trichloroacetonitrile yields alkyl 4-mino-6-methyl-2-trichloromethylpyrimidine-5-carboxylates. The latter compounds react with aryl isocyanates to produce the corresponding pyrimidinylureas, which undergo cyclization to 3-aryl-5-methyl-7-trichloromethylpyrimido[4,5- d]pyrimidine-2,4(1H,3H)-diones under the action of MeONa in MeOH.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. A. Voronkova, A. V. Komkov & V. A. Dorokhov

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  1. V. A. Voronkova
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  2. A. V. Komkov
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  3. V. A. Dorokhov
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Correspondence to V. A. Dorokhov.

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On the occasion of the 75th anniversary of the foundation of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 347–351, February, 2009.

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Voronkova, V.A., Komkov, A.V. & Dorokhov, V.A. Synthesis of trichloromethylpyrimidines and trichloromethylpyrimido [4,5-d]pyrimidines from alkyl 2-(diaminomethylidene)-3-oxobutyrates and trichloroacetonitrile. Russ Chem Bull 58, 351–355 (2009). https://doi.org/10.1007/s11172-010-0015-5

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  • DOI: https://doi.org/10.1007/s11172-010-0015-5

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