SYNTHESIS AND MOLECULAR STRUCTURE OF 4-{[6-((2<i>SR</i>,4<i>SR</i>)-4-ACETYL-4-METHYLPYRROLIDIN-2-YL)-2-(4-CYANOPHENOXY)PYRIMIDIN- 4-YL]OXY}-3,5-DIMETHYLBENZONITRILE AND 4-[(6-{(2<i>SR</i>,4<i>SR</i>)-4-ACETYL-1-[(4-BROMOPHENYL)SULFONYL]-4-METHYLPYRROLIDIN-2-YL}-2-(4-CYANOPHENOXY)PYRIMIDIN-4-YL)OXY]-3,5-DIMETHYLBENZONITRILE

Authors

  • Никита А. Соколов Faculty of Chemistry, Lomonosov Moscow State University 1, Build. 3 Leninskie Gory, Moscow 119991, Russia
  • Владимир Н. Иванов Faculty of Chemistry, Lomonosov Moscow State University 1, Build. 3 Leninskie Gory, Moscow 119991, Russia
  • Ильдар Р. Юсупов Faculty of Chemistry, Lomonosov Moscow State University 1, Build. 3 Leninskie Gory, Moscow 119991, Russia
  • Антон В. Ясевич Faculty of Chemistry, Lomonosov Moscow State University 1, Build. 3 Leninskie Gory, Moscow 119991, Russia
  • Артем В. Трубников Faculty of Chemistry, Lomonosov Moscow State University 1, Build. 3 Leninskie Gory, Moscow 119991, Russia
  • Юлия В. Ульянова D. Mendeleyev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047, Russia
  • Константин А. Лысенко Faculty of Chemistry, Lomonosov Moscow State University 1, Build. 3 Leninskie Gory, Moscow 119991, Russia
  • Александр В. Куркин Faculty of Chemistry, Lomonosov Moscow State University 1, Build. 3 Leninskie Gory, Moscow 119991, Russia

DOI:

https://doi.org/10.1007/6518

Keywords:

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

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.

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Published

2022-01-27

Issue

Vol. 58 No. 1 (2022)

Section

Short Communications