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Chemoselective Synthesis of 4,5‐Diarylpyrrolo[2,3‐ d ]pyrimidines (6,7‐Diaryl‐7‐deazapurines) by Consecutive Suzuki and Liebeskind–Srogl Cross‐Couplings
Author(s) -
Krömer Matouš,
Klečka Martin,
Slavětínská Lenka,
Klepetářová Blanka,
Hocek Michal
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402882
Subject(s) - chemistry , suzuki reaction , aryl , pyrimidine , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , palladium , alkyl
A new chemoselective synthesis of pyrrolo[2,3‐ d ]pyrimidines (7‐deazapurines) bearing two different aryl groups at positions 4 and 5 was developed based on two orthogonal cross‐couplings. Starting from 7‐benzyl‐protected 4‐(phenylsulfanyl)‐5‐iodopyrrolo[2,3‐ d ]pyrimidine, the Pd‐catalyzed Suzuki coupling with arylboronic acids proceeded selectively at position 5, followed by the Pd‐catalyzed Cu‐mediated Liebeskind–Srogl coupling at position 4. A small library of 4,5‐diaryl derivatives was prepared.