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Facile Synthesis of 2‐Amino‐4‐alkoxypyrimidines via Consecutive Nucleophilic Aromatic Substitution ( S N Ar ) Reactions
Author(s) -
Kim Juhyeon,
Cho Yong Seo,
Min SunJoon
Publication year - 2016
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11014
Subject(s) - nucleophilic aromatic substitution , nucleophilic substitution , radical nucleophilic aromatic substitution , substitution reaction , chemistry , substitution (logic) , electrophilic aromatic substitution , sni , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , acid hydrolysis , computer science , hydrolysis , programming language
A transition‐metal‐free and regioselective synthesis of a series of 2‐amino‐4‐alkoxypyrimidines is described. The S N Ar alkoxylation of 2,4‐dichloropyrimidines regioselectively provided 2‐chloro‐4‐alkoxypyrimidines, which were subsequently subject to the second S N Ar amination with cyclic amines in the presence of triethylamine at high temperature to afford 2‐amino‐4‐alkoxypyrimidines in good overall yield.