Efficient Synthesis of 4- and 5-Substituted 2-Aminopyrimidines by Coupling of [beta]-Chlorovinyl Aldehydes and Guanidines

A general, practical, and simple synthesis of functionalized 2-aminopyrimidines starting from [beta]-chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently transformed into the pyrimidine derivatives by a two-step sequence involv...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2017; no. 29; p. 4260
Main Authors Komendantova, Anna S, Komkov, Alexander V, Volkova, Yulia A, Zavarzin, Igor V
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.08.2017
Subjects
Aldehydes
Anticancer properties
Column chromatography
Condensates
Guanidines
Ketones
Potassium
Potassium carbonate
Pyrimidines
Reagents
Synthesis
Vilsmeier-Haack reaction
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Summary:A general, practical, and simple synthesis of functionalized 2-aminopyrimidines starting from [beta]-chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently transformed into the pyrimidine derivatives by a two-step sequence involving the Vilsmeier-Haack reaction followed by a condensation reaction with guanidines. The protocol is distinguished by operational simplicity, inexpensive reagents, and functional-group tolerance. In many cases, pure solid products can be obtained in high to excellent yields without using column chromatography. The synthetic value of the method was demonstrated by the efficient synthesis of steroidal pyrimidines and a precursor of the antitumor agents Imatinib and Mocetinostat.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700737