Facile Synthesis of 2-Amino-4-alkoxypyrimidines via Consecutive Nucleophilic Aromatic Substitution (SNAr) Reactions

A transition‐metal‐free and regioselective synthesis of a series of 2‐amino‐4‐alkoxypyrimidines is described. The SNAr alkoxylation of 2,4‐dichloropyrimidines regioselectively provided 2‐chloro‐4‐alkoxypyrimidines, which were subsequently subject to the second SNAr amination with cyclic amines in th...

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Published inBulletin of the Korean Chemical Society Vol. 37; no. 12; pp. 1998 - 2008
Main Authors Kim, Juhyeon, Cho, Yong Seo, Min, Sun-Joon
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag GmbH & Co. KGaA 01.12.2016
Wiley‐VCH Verlag GmbH & Co. KGaA
대한화학회
Subjects
2-Amino-4-alkoxypyrimidines
Alkoxylation
Amination
Nucleophilic aromatic substitution
Regioselectivity
화학
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Summary:A transition‐metal‐free and regioselective synthesis of a series of 2‐amino‐4‐alkoxypyrimidines is described. The SNAr alkoxylation of 2,4‐dichloropyrimidines regioselectively provided 2‐chloro‐4‐alkoxypyrimidines, which were subsequently subject to the second SNAr amination with cyclic amines in the presence of triethylamine at high temperature to afford 2‐amino‐4‐alkoxypyrimidines in good overall yield.
Bibliography:Ministry of Health & Welfare, Republic of Korea - No. HI16C1677
ark:/67375/WNG-SMR70CX1-Z
ArticleID:BKCS11014
istex:27B8DA6725FE3CBC975FFC266C0A02DC94A8C65D
Supporting Information
Korea Health Industry Development Institute - No. KHIDI
Hanyang University - No. HY-2015-N
G704-000067.2016.37.12.005
http://onlinelibrary.wiley.com/doi/10.1002/bkcs.11014/abstract
ISSN:1229-5949
0253-2964
1229-5949
DOI:10.1002/bkcs.11014