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Molecules 2012, 17(5), 5363-5384; doi:10.3390/molecules17055363
Article

Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides

1, 1, 1, 1, 2, 1 and 1,*
1 Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, 1000 Ljubljana, Slovenia 2 Boehringer Ingelheim Pharma GmbH & Co. KG, Medicinal Chemistry, 88397 Biberach, Germany
* Author to whom correspondence should be addressed.
Received: 20 March 2012 / Revised: 24 April 2012 / Accepted: 26 April 2012 / Published: 8 May 2012
(This article belongs to the Special Issue Parallel Synthesis)
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Abstract

A library of 24 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides 10{1,2; 1–12} was prepared by a parallel solution-phase approach. The synthesis comprises a five-step transformation of itaconic acid (11) into 1-methyl and 1-phenyl substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxylic acids 17{1,2} followed by parallel amidation of 17{1,2} with a series of 12 aliphatic amines 18{1–12} to afford the corresponding carboxamides 10 in good overall yields and in 80–100% purity.
Keywords: parallel synthesis; pyrimidines; 2-(heteroaryl)ethylamines parallel synthesis; pyrimidines; 2-(heteroaryl)ethylamines
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Črček, B.; Baškovč, J.; Grošelj, U.; Kočar, D.; Dahmann, G.; Stanovnik, B.; Svete, J. Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides. Molecules 2012, 17, 5363-5384.

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