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DOI: 10.1055/s-0034-1379547
Synthesis of 6-Alkyl-7-oxo-4,5,6,7-tetrahydropyrazolo[1,5-c]pyrimidine-3-carboxamides
Publikationsverlauf
Received: 26. September 2014
Accepted after revision: 29. Oktober 2014
Publikationsdatum:
24. November 2014 (online)
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Abstract
Two variants of the synthesis of 6-alkyl-7-oxo-4,5,6,7-tetrahydropyrazolo[1,5-c]pyrimidine-3-carboxamides have been developed. The first pathway comprises nine steps starting with the introduction of the 6-alkyl group (R1) via addition of a primary alkylamine to methyl acrylate followed by a seven-step transformation into the 6-benzyl-7-oxo-4,5,6,7-tetrahydropyrazolo[1,5-c]pyrimidine-3-carboxylic acid, which is then amidated into title compounds. The other variation is based on an analogous four-step transformation of Boc-β-alanine into a 6-unsubstituted benzyl ester as the key intermediate. The 6-alkyl group (R1) is then introduced by N-alkylation with alkyl halides, followed by O-debenzylation to give the carboxylic acids, and amidation. A library of 18 title carboxamides was prepared in very good yields.
Key words
histamine analogues - pyrazolo[1,5-c]pyrimidines - parallel synthesis - cyclization - amidationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379547. Included are 1H and 13C NMR spectra of compounds 3 and 5–9.
- Supporting Information
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