Parallel synthesis of 7-heteroaryl-pyrazolo[1,5-a]pyrimidine-3-carboxamides

Molecular Diversity - Tập 17 - Trang 731-743 - 2013
Sizana Ahmetaj1, Nina Velikanje1, Uroš Grošelj1, Ines Šterbal1, Benjamin Prek1, Amalija Golobič1, Drago Kočar1, Georg Dahmann2, Branko Stanovnik1, Jurij Svete1
1Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana, Slovenia
2Medicinal Chemistry, Boehringer Ingelheim Pharma GmbH & Co. KG, Biberach, Germany

Tóm tắt

A simple and practical four-step protocol for the parallel synthesis of 7-heteroaryl-pyrazolo[1,5- $$a$$ ]pyrimidine-3-carboxamides was developed. The synthesis starts with transformation of commercially available 2-acetylpyridine and acetylpyrazine with $$N,$$ $$N$$ -dimethylformamide dimethylacetal into the corresponding $$(E)$$ -3-(dimethylamino)-1-(heteroaryl)prop-2-en-1-ones followed by cyclisation with methyl 5-amino-1 $$H$$ -pyrazole-4-carboxylate to give methyl 7-heteroarylpyrazolo[1,5- $$a$$ ]pyrimidine-3-carboxylates. Hydrolysis of the ester group and subsequent amidation of the so formed carboxylic acids with 12 primary and secondary aliphatic amines furnished a library of 24 title compounds in good overall yields and purity.

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