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N-alkylation of substituted pyrazoles and pyrazolo[3,4-d]pyrimidines with dimethylformamide diethyl acetal or triethyl orthoformate

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The N-alkylation of some substituted pyrazoles and pyrazolo[3,4-d]pyrimidines with dimethylformamide diethyl acetal or triethyl orthoformate has been examined. Dimethylformamide diethyl acetal is more effective as an alkylating agent than triethyl orthoformate. Alkylation of 3-methoxycarbonylpyrazole gives a mixture of N-1- and N-2-ethyl derivatives. Alkylation of pyrazolo[3,4-d]pyrimidines takes place at the 1-position of the pyrazole ring only. In the case of thio-derivatives of pyrazolo[3,4-d]pyrimidines, S-alkylation occurs in addition to N-alkylation.

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Authors and Affiliations

  1. All-Union Scientific Center for Oncology, Academy of Medical Sciences of the USSR, 115478, Moscow

    Yu. N. Bulychev, M. N. Preobrazhenskaya, A. I. Chernyshev & S. E. Esipov

  2. All-Union Research Institute for Antibiotics, Minmedmikrobioprom USSR, 113105, Moscow

    Yu. N. Bulychev, M. N. Preobrazhenskaya, A. I. Chernyshev & S. E. Esipov

Authors
  1. Yu. N. Bulychev
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  2. M. N. Preobrazhenskaya
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  3. A. I. Chernyshev
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  4. S. E. Esipov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 914–919, July, 1988.

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Bulychev, Y.N., Preobrazhenskaya, M.N., Chernyshev, A.I. et al. N-alkylation of substituted pyrazoles and pyrazolo[3,4-d]pyrimidines with dimethylformamide diethyl acetal or triethyl orthoformate. Chem Heterocycl Compd 24, 751–755 (1988). https://doi.org/10.1007/BF00633169

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  • DOI: https://doi.org/10.1007/BF00633169

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