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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

Никита А. Соколов, Владимир Н. Иванов, Ильдар Р. Юсупов, Антон В. Ясевич, Артем В. Трубников, Юлия В. Ульянова, Константин А. Лысенко, Александр В. Куркин
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Abstract


A novel diarylpyrimidine derivative, 4-{[6-((2SR,4SR)-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-{(2SR,4SR)-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.

Keywords


diarylpyrimidines; aza-Cope/Mannich tandem reaction; HIV; non-nucleoside reverse transcriptase inhibitors; [3,3]-sigmatropic rearrangements; X-ray structural analysis.

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