Modification of Pyrrolo[2,3-d]pyrimidines by C-H Borylation Followed by Cross-Coupling or Other Transformations: Synthesis of 6,8-Disubstituted 7-Deazapurine Bases

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10315848" target="_blank" >RIV/00216208:11310/15:10315848 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/15:00454228
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201501177" target="_blank" >http://dx.doi.org/10.1002/ejoc.201501177</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201501177" target="_blank" >10.1002/ejoc.201501177</a>

Result language
angličtina
Original language name
Modification of Pyrrolo[2,3-d]pyrimidines by C-H Borylation Followed by Cross-Coupling or Other Transformations: Synthesis of 6,8-Disubstituted 7-Deazapurine Bases
Original language description
A general access to 4-substituted 6-arylpyrrolo[2,3-d]pyrimidine (6-substituted 8-aryl-7-deazapurine derivatives) was developed based on iridium-catalyzed C-H borylations of pyrrolo[2,3-d]pyrimidines at the 6-position followed by the Suzuki cross-coupling reactions or other functional group transformations of the boronates. Biologically relevant 6-arylpyrrolo[2,3-d]pyrimidin-4-amines (8-aryl-7-deazaadenines) and pyrrolo[2,3-d]pyrimidin-4-ones (-7-deazahypoxanthines) were synthesized starting from SEM-protected 4-methylsulfanyl- or 4-methoxypyrrolo[2,3-d]pyrimidine. The one-pot borylation/Suzuki coupling reactions were followed either by demethylation and deprotection to yield deazahypoxanthine bases, or by oxidation of sulfide to sulfone, amination anddeprotection to give deazaadenines. In addition, the boronate intermediates were converted into 6-halo- or 6-(trifluoromethyl)pyrrolo[2,3-d]pyrimidine (8-halo- or 8-trifluoromethyl-7-deazapurine) derivatives.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—

Project
<a href="/en/project/GAP207%2F12%2F0205" target="_blank" >GAP207/12/0205: Development of novel methodologies of C-H activations of purines, deazapurines, pyrimidines and related heterocycles</a><br>
Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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