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Synthesis of N-Alkylated Derivatives of Pyrazolo[1,5-a]pyrimidine and Their Reaction with Methylamine

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

With the object of studying the factors influencing the course of enamine rearrangements, we have carried out the N-alkylation of alkyl- and aryl-substituted pyrazolo[1,5-a]pyrimidines. Using the NOEDIF NMR spectroscopic method for the cases of 5,7-dimethyl-2-phenyl- and 2,5,7-triphenylpyrazolo[1,5-a]pyrimidines it was found that addition of the alkyl group occurs at the N(4) atom of the pyrimidine fragment in the pyrazolo[1,5-a]pyrimidine. It was shown that, when reacting with an alcoholic solution of methylamine, the 5,7-dimethyl-2-phenyl- and 2,5,7-triphenylpyrazolo[1,5-a]pyrimidine iodomethylates undergo decomposition to give 5-methylamino-3-phenylpyrazole and 5-(1,3-diphenyl-3-methylamino-2-propenylid-1-ene)amino-3-phenylpyrazole.

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Authors and Affiliations

  1. National Academy of Sciences, Institute of Organic Chemistry, Yerevan, 375094, Armenian Republic

    G. G. Danagulyan & A. P. Boyakhchyan

  2. Center of Molecular Structure Investigation, National Academy of Sciences, Yerevan, 375014, Armenian Republic

    G. A. Panosyan

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  1. G. G. Danagulyan
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  2. G. A. Panosyan
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  3. A. P. Boyakhchyan
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Danagulyan, G.G., Panosyan, G.A. & Boyakhchyan, A.P. Synthesis of N-Alkylated Derivatives of Pyrazolo[1,5-a]pyrimidine and Their Reaction with Methylamine. Chemistry of Heterocyclic Compounds 38, 581–585 (2002). https://doi.org/10.1023/A:1019517414682

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