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Synthesis 2017; 49(20): 4623-4650
DOI: 10.1055/s-0036-1588443
DOI: 10.1055/s-0036-1588443
special topic
Synthesis of 2,6-Substituted 7-(Het)aryl-7-deazapurine Nucleobases (2,4-Disubstituted 5-(Het)aryl-pyrrolo[2,3-d]pyrimidines)
This work was supported by the Academy of Sciences of the Czech Republic (RVO 61388963 and the Praemium Academiae award to M. Hocek), by the Czech Science Foundation (16-0011785 to N. S. and M. H.), by the Czech Health Research Council (15-31984A to S. S.), and by Gilead Sciences, Inc.Further Information
Publication History
Received: 29 March 2017
Accepted after revision: 02 May 2017
Publication Date:
20 June 2017 (online)
Published as part of the Special Topic Modern Strategies for Heterocycles Synthesis
Abstract
A series of 7-(het)aryl-7-deazapurine nucleobases (5-[(het)aryl]-2,4-disubstituted 7H-pyrrolo[2,3-d]pyrimidines) bearing NH2, OMe, SMe, or Me groups at position 6 and H, NH2, or Me at position 2 were prepared by the aqueous Suzuki–Miyaura cross-coupling reactions from SEM-protected 7-iodo-7-deazapurines with (het)arylboronic acids followed by deprotection. The 6-methoxy derivatives were further transformed into 7-deazahypoxanthines or 7-deazaguanines by O-demethylation reactions. Unlike their ribonucleoside counterparts, the 7-deazapurine nucleobases did not exert any significant cytostatic or antiviral effects.
Key words
deazapurines - pyrrolo[2,3-d]pyrimidines - nucleobases - Suzuki–Miyaura cross-coupling - deprotection - demethylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588443.
- Supporting Information
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