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
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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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
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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
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