New Pyrimidylboronic Acids and Functionalized Heteroarylpyrimidines by Suzuki Cross‐Coupling Reactions | Zendy

Clapham Kate M. | Zendy; Smith Amy E. | Zendy; Batsanov Andrei S. | Zendy; McIntyre Laura | Zendy; Pountney Adam | Zendy; Bryce Martin R. | Zendy; Tarbit Brian | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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)

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research