Chemoselective Reactions of 4,6-Dichloro-2-(methylsulfonyl)pyrimidine and Related Electrophiles with Amines

Chemoselective S-NAr reactions of 4,6-dichloro-2-(methylsulfonyl)pyrimidine and several related electrophiles with amines and their derivatives are described. In the presence of weak bases anilines and secondary aliphatic amines selectively displace the chloride group. Deprotonated anilines and thei...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 45; no. 13; pp. 1764 - 1784
Main Authors Baiazitov, Ramil, Du, Wu, Lee, Chang-Sun, Hwang, Seongwoo, Almstead, Neil G., Moon, Young-Choon
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.2013
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2,4,6-TRICHLOROPYRIMIDINE
chemoselectivity
PYRIMIDINE-DERIVATIVES
REGIOSELECTIVE 4-AMINO-DE-CHLORINATION
DISCOVERY
heterocycles
BIOLOGICAL EVALUATION
chloride
AGENTS
INHIBITORS
ANTAGONISTS
pyrimidine
sulfone
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Summary:Chemoselective S-NAr reactions of 4,6-dichloro-2-(methylsulfonyl)pyrimidine and several related electrophiles with amines and their derivatives are described. In the presence of weak bases anilines and secondary aliphatic amines selectively displace the chloride group. Deprotonated anilines and their carbonyl derivatives displace the sulfone group. Sterically and electronically unbiased primary aliphatic amines selectively displace the sulfone group in 4,6-dichloro-2-(methylsulfonyl)pyrimidine; however, their reactions with other electrophiles generally are less selective. Steric-driven selectivity explanation was proposed.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0033-1338853