- Efficient synthesis of 4- And 5-substituted 2-aminopyrimidines by coupling of β-Chlorovinyl Aldehydes and Guanidines
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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, Anna S.,Komkov, Alexander V.,Volkova, Yulia A.,Zavarzin, Igor V.
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supporting information
p. 4247 - 4254
(2018/08/24)
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- A One-Pot Synthesis of 2-Aminopyrimidines from Ketones, Arylacetylenes, and Guanidine
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The three-component reaction of ketones, arylacetylenes, and guanidine catalyzed by the KOBut/DMSO system leads to 2-aminopyrimidines in up to 80% yield. Depending on structure of the starting ketones, the aromatization of intermediate dihydropyrimidines occurs either with loss of hydrogen molecules or methylbenzenes. The latter process takes place in the ketones, in which one of the substituents is not a methyl group. The reaction conditions are tolerable for dialkyl-, aryl(hetaryl) alkyl-, and cycloalkyl ketones.
- Schmidt, Elena Yu.,Tatarinova, Inna V.,Protsuk, Nadezhda I.,Ushakov, Igor A.,Trofimov, Boris A.
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p. 119 - 125
(2017/04/26)
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- 2-Aminopyrimidines in just two steps from ketones, acetylenes and guanidine via β,γ enones
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Available β,γ-enones, the products of nucleophilic addition of ketones to phenylacetylene, react with guanidine in the KOH / DMSO system at 70?°C to give 2-aminopyrimidines in up to 72% yield.
- Schmidt, Elena Yu.,Tatarinova, Inna V.,Ivanova, Elena V.,Trofimov, Boris A.
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p. 283 - 284
(2017/06/06)
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