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Regioselective Control of the SNAr Amination of 5-Substituted-2,4-Dichloropyrimidines Using Tertiary Amine Nucleophiles

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F15%3A33156151" target="_blank" >RIV/61989592:15310/15:33156151 - isvavai.cz</a>

  • Result on the web

    <a href="http://pubs.acs.org/doi/full/10.1021/acs.joc.5b01044" target="_blank" >http://pubs.acs.org/doi/full/10.1021/acs.joc.5b01044</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acs.joc.5b01044" target="_blank" >10.1021/acs.joc.5b01044</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Regioselective Control of the SNAr Amination of 5-Substituted-2,4-Dichloropyrimidines Using Tertiary Amine Nucleophiles

  • Original language description

    The SnAr reaction of 2,4-dichloropyrimidines,further substituted with an electron-withdrawing substituent at C-5, has selectivity for substitution at C-4. Here we report that tertiary amine nucleophiles show excellent C-2 selectivity. In situ N-dealkylation of an intermediate gives the product that formally corresponds to the reaction of a secondary amine nucleophile at C-2. This reaction is practical (fast under simple reaction conditions, with good generality for tertiary amine structure and moderateto excellent yields) and significantly expands access to pyrimidine structures.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

    <a href="/en/project/EE2.4.31.0130" target="_blank" >EE2.4.31.0130: Development and bolstering of cooperation among academic and commercial institutions with focuse on chemical and pharmaceutical research</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Others

  • Publication year

    2015

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Journal of Organic Chemistry

  • ISSN

    0022-3263

  • e-ISSN

  • Volume of the periodical

    80

  • Issue of the periodical within the volume

    15

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    7

  • Pages from-to

    7757-7763

  • UT code for WoS article

    000359393500048

  • EID of the result in the Scopus database