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

doi:10.3390/molecules17055363

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

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

Bojana Črček¹, Jernej Baškovč¹, Uroš Grošelj¹, Drago Kočar¹, Georg Dahmann², Branko Stanovnik¹ and Jurij Svete^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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(5):5363-5384.

Chicago/Turabian Style

Črček, Bojana; Baškovč, Jernej; Grošelj, Uroš; Kočar, Drago; Dahmann, Georg; Stanovnik, Branko; Svete, Jurij. 2012. "Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides." Molecules 17, no. 5: 5363-5384.

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