Efficient Synthesis of 4- and 5-Substituted 2-Aminopyrimidines by Coupling of β-Chlorovinyl Aldehydes and Guanidines

Efficient Synthesis of 4- and 5-Substituted 2-Aminopyrimidines by Coupling of β-Chlorovinyl Aldehydes and Guanidines Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2017, Volume: 2017, Number: 29, Pages: 4260-4264 Pages count : 5 DOI: 10.1002/ejoc.201700737

Authors

Komendantova Anna S. ¹ , Komkov Alexander V. ¹ , Volkova Yulia A. ¹ , Zavarzin Igor V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia

A general, practical, and simple synthesis of functionalized 2-aminopyrimidines starting from β-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.

Komendantova A.S. , Komkov A.V. , Volkova Y.A. , Zavarzin I.V.
Efficient Synthesis of 4- and 5-Substituted 2-Aminopyrimidines by Coupling of β-Chlorovinyl Aldehydes and Guanidines
European Journal of Organic Chemistry. 2017. V.2017. N29. P.4260-4264. DOI: 10.1002/ejoc.201700737 WOS Scopus OpenAlex

≡ Web of science:	WOS:000407167300007
≡ Scopus:	2-s2.0-85040462667
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