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Journal of Zhejiang University SCIENCE B 2010 Vol.11 No.2 P.94-101

http://doi.org/10.1631/jzus.B0900293


A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular SNAr sequence


Author(s):  Hai-feng WU, Pei-zhi ZHANG, Jun WU

Affiliation(s):  Department of Chemistry, Zhejiang University, Hangzhou 310027, China; more

Corresponding email(s):   wujunwu@zju.edu.cn

Key Words:  Reductive amination/intermolecular SNAr, C-O and C-N bonds, Amine, Pyrimidine, Herbicide


Hai-feng WU, Pei-zhi ZHANG, Jun WU. A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular SNAr sequence[J]. Journal of Zhejiang University Science B, 2010, 11(2): 94-101.

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author="Hai-feng WU, Pei-zhi ZHANG, Jun WU",
journal="Journal of Zhejiang University Science B",
volume="11",
number="2",
pages="94-101",
year="2010",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.B0900293"
}

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%T A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular SNAr sequence
%A Hai-feng WU
%A Pei-zhi ZHANG
%A Jun WU
%J Journal of Zhejiang University SCIENCE B
%V 11
%N 2
%P 94-101
%@ 1673-1581
%D 2010
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.B0900293

TY - JOUR
T1 - A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular SNAr sequence
A1 - Hai-feng WU
A1 - Pei-zhi ZHANG
A1 - Jun WU
J0 - Journal of Zhejiang University Science B
VL - 11
IS - 2
SP - 94
EP - 101
%@ 1673-1581
Y1 - 2010
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.B0900293


Abstract: 
A novel tandem reductive amination/intermolecular nucleophilic aromatic substitution (SNAr) sequence has been established for the synthesis of amine containing pyrimidine in formation of one carbon-oxygen and one carbon-nitrogen bonds in a one-pot fashion. Treatment of aldehyde with arylamine, 2-methanesulfonyl-4,6-dimethoxypyrimidine and sodium borohydride provides good overall yield. The p-toluenesulfonic acid (PTSA) can be used as activator and is generally needed in the reaction. Dioxane is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran (THF), MeCN, toluene and dichloromethane. The procedure is carried out effectively in the presence of K2CO3. The reaction proceeds smoothly with aromatic aldehydes and arylamines possessing electron-donating or -withdrawing groups. This method can be applied to the synthesis of the oilseed rape herbicide and is superior to the classical one in several aspects: cutting out several purification steps, minimizing solvent use and chemical waste, and saving time. Its advantages such as operational convenience, high-efficient synthesis, and starting material availability make it a desirable method for preparing amines with molecular diversity and biological activity.

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Reference

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