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New Pyrimidylboronic Acids and Functionalized Heteroarylpyrimidines by Suzuki Cross‐Coupling Reactions
Author(s) -
Clapham Kate M.,
Smith Amy E.,
Batsanov Andrei S.,
McIntyre Laura,
Pountney Adam,
Bryce Martin R.,
Tarbit Brian
Publication year - 2007
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.200700654
Subject(s) - chemistry , benzothiazole , pyrazine , suzuki reaction , coupling reaction , reactivity (psychology) , pyridine , halogen bond , medicinal chemistry , halide , thiophene , quinoline , halogen , hydrogen bond , organic chemistry , polymer chemistry , combinatorial chemistry , catalysis , molecule , palladium , medicine , alkyl , alternative medicine , pathology
We report the synthesis of 2‐chloro‐5‐pyrimidylboronic acid ( 6 ) and 2‐amino‐5‐pyrimidylboronic acid ( 8 ) by lithium–halogen exchange followed by reaction with triisopropylborate. Their reactivity with heteroaryl halides in Suzuki–Miyaura cross‐coupling reactions has been evaluated. New highly functionalized 5‐heteroarylpyrimidine derivatives 24 – 33 (heteroaryl = quinoline, pyridine, pyrimidine, pyrazine, thiophene, benzothiazole) have been obtained in synthetically useful yields. The X‐ray structure of 6 reveals extensive intermolecular O–H ··· N hydrogen bonding in the crystal. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)