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Synthesis of 2-substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidin-4(3H)-ones
Uros Groselj (1)
, Georg Dahmann (2) , Branko Stanovnik (3) , Jurij Svete (4,*) (1) Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana, SI-1000, Slovenia
(2) Medicinal Chemistry, Boehringer-Ingelheim Pharma GmbH & Co. KG, Biberach, D-88397, Germany
(3) Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana, SI-1000, Slovenia
(4) Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana, SI-1000, Slovenia
(*) Corresponding Author
Received: 19 Dec 2012 | Revised: 07 Jan 2013 | Accepted: 08 Jan 2013 | Published: 31 Mar 2013 | Issue Date: March 2013
Abstract
2-Substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidin-4(3H)-ones were synthesized in three steps from itaconic acid derivatives via cyclization with primary amines followed by Masamune-Claisen condensation, and cyclization of the newly formed β-keto esters with amidines. Preparation and/or isolation of β-keto esters with polar N-substituents failed, but the corresponding final products were obtained in a different way. 6-(1-(3-Hydroxypropyl)-5-oxopyrrolidin-3-yl)-2-phenylpyrimidin-4(3H)-one was obtained by hydrogenolytic o-deprotection of its o-benzyl derivative. Depending on reaction conditions, further mesylation of 6-(1-(3-(benzyloxy)propyl)-5-oxopyrrolidin-3-yl)-2-phenylpyrimidin-4(3H)-one followed by treatment with pyrrolidine gave either the monoaminated- or the diaminated product. The structures of novel compounds were determined by NMR.
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DOI: 10.5155/eurjchem.4.1.1-6.718
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Funding information
Boehringer-Ingelheim Pharma GmbH & Co. KG (Biberach, Germany) and Slovenian Research Agency (Ljubljana, Slovenia) (Grant No: P1-0179).
Citations
[1]. Zhaohua Wan, Dan Wang, Zixuan Yang, Heng Zhang, Shengchun Wang, Aiwen Lei
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DOI: 10.1039/D0GC00687D
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DOI Link: https://doi.org/10.5155/eurjchem.4.1.1-6.718
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European Journal of Chemistry 2013, 4(1), 1-6 | doi: https://doi.org/10.5155/eurjchem.4.1.1-6.718 | Get rights and content
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