A chemoselective aniline–chloropyrimidine coupling in a competing electrophilic environment

A highly chemoselective substitution on 4-amino-6-chloropyrimidine ring system having a competing aldehyde functionality has been realized with anilines which produces 4, 6-diaminopyrimidine-5-carbaldehyde in high yield. The reaction may involve the intermediacy of imines. A variety of aromatic amin...

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Bibliographic Details
Published inTetrahedron letters Vol. 49; no. 1; pp. 102 - 105
Main Authors Choudhury, Anusuya, Chen, Hongfeng, Nilsen, Christopher N., Sorgi, Kirk L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 2008
Elsevier
Subjects
Acid catalyzed coupling
Chemistry
Chemistry, Organic
Chloropyrimidine
Diaminopyrimidines
Physical Sciences
Science & Technology
Acid catalyzed coupling
Chloropyrimidine
Diaminopyrimidines
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Summary:A highly chemoselective substitution on 4-amino-6-chloropyrimidine ring system having a competing aldehyde functionality has been realized with anilines which produces 4, 6-diaminopyrimidine-5-carbaldehyde in high yield. The reaction may involve the intermediacy of imines. A variety of aromatic amines participate in this reaction successfully to generate diaminopyrimidine aldehydes in moderate to high yield.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.11.009