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Issue 4, 2019
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Silver-promoted selective fluorination of 2-aminopyrimidines: synthesis of 5-fluoro-2-aminopyrimidine derivatives

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Abstract

Selective fluorination of 4-substituted 2-aminopyrimidine derivatives with Selectfluor in the presence of Ag2CO3 is presented. The substrates are 4-aryl- or vinyl- or amine-substituted 2-aminopyrimidines. This method gives 4-substituted 5-fluoro-2-aminopyrimidines in fair to high yields with excellent regioselectivities. 5-Fluoro-4-(pyridin-3-yl)-2-aminopyrimidine was transformed into 5-fluoro-N-(2-methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine in the synthesis of fluorinated imatinib base.

Graphical abstract: Silver-promoted selective fluorination of 2-aminopyrimidines: synthesis of 5-fluoro-2-aminopyrimidine derivatives

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Supplementary files

Article information


Submitted
30 Sep 2018
Accepted
09 Nov 2018
First published
12 Nov 2018

Org. Chem. Front., 2019,6, 426-431
Article type
Research Article

Silver-promoted selective fluorination of 2-aminopyrimidines: synthesis of 5-fluoro-2-aminopyrimidine derivatives

M. Zhao, J. Cai and X. Zhao, Org. Chem. Front., 2019, 6, 426
DOI: 10.1039/C8QO01054D

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