Synthesis and molecular structure of 4-{[6-((2SR,4SR)-4-acetyl-4-methylpyrrolidin-2-yl)-2-(4-cyanophenoxy)pyrimidin-4-yl]oxy}-3,5-dimethylbenzonitrile and 4-[(6-{(2SR,4SR)-4-acetyl-1-[(4-bromophenyl)sulfonyl]-4-methylpyrrolidin-2-yl}-2-(4-cyanophenoxy)pyrimidin-4-yl)oxy]-3,5-dimethylbenzonitrile

A novel diarylpyrimidine derivative, 4-{[6-((2 SR ,4 SR )-4-acetyl-4-methylpyrrolidin-2-yl)-2-(4-cyanophenoxy)pyrimidin-4-yl]oxy}- 3,5-dimethylbenzonitrile containing a pyrrolidine moiety at position 6 of the pyrimidine ring was obtained as a result of the tandem aza- Cope/Mannich reaction between 4...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2022, Vol.58 (1), p.64-67
Main Authors: Sokolov, Nikita А., Ivanov, Vladimir N., Iusupov, Ildar R., Iasevich, Anton V., Trubnikov, Artem V., Ulianova, Yuliya V., Lyssenko, Konstantin А., Kurkin, Alexander V.
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chlorides
Dichloromethane
Molecular structure
Organic Chemistry
Pharmacy
Short Communications
Structural analysis
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Summary:A novel diarylpyrimidine derivative, 4-{[6-((2 SR ,4 SR )-4-acetyl-4-methylpyrrolidin-2-yl)-2-(4-cyanophenoxy)pyrimidin-4-yl]oxy}- 3,5-dimethylbenzonitrile containing a pyrrolidine moiety at position 6 of the pyrimidine ring was obtained as a result of the tandem aza- Cope/Mannich reaction between 4-{[2-(4-cyanophenoxy)-6-formylpyrimidin-4-yl]oxy}-3,5-dimethylbenzonitrile and 1-amino- 2,3-dimethylbut-3-en-2-ol in methylene chloride in the presence of 10-camphorsulfonic acid. The structure of the product of its reaction with 4-bromobenzenesulfonyl chloride, 4-[(6-{(2 SR ,4 SR )-4-acetyl-1-[(4-bromophenyl)sulfonyl]-4-methylpyrrolidin-2-yl}-2-(4-cyanophenoxy) pyrimidin-4-yl)oxy]-3,5-dimethylbenzonitrile, was investigated by X-ray structural analysis.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-022-03057-y