Nucleophilic Substitution Reaction of Pyrimidin-2-yl Phosphates Using Amines and Thiols as Nucleophiles Mediated by PEG-400 as an Environmentally Friendly Solvent

Ting Xing; Kai-Jie Wei; Zheng-Jun Quan; Xi-Cun Wang

doi:10.1055/s-0035-1560175

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(24): 3925-3935
DOI: 10.1055/s-0035-1560175

paper

Nucleophilic Substitution Reaction of Pyrimidin-2-yl Phosphates Using Amines and Thiols as Nucleophiles Mediated by PEG-400 as an Environmentally Friendly Solvent

Ting Xing

^aKey Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Gansu 730070, P. R. of China

^bKey Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Gansu 730070, P. R. of China eMail: wangxicun@nwnu.edu.cn

,

Kai-Jie Wei

^aKey Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Gansu 730070, P. R. of China

^bKey Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Gansu 730070, P. R. of China eMail: wangxicun@nwnu.edu.cn

,

Zheng-Jun Quan*

^aKey Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Gansu 730070, P. R. of China

^bKey Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Gansu 730070, P. R. of China eMail: wangxicun@nwnu.edu.cn

,

Xi-Cun Wang*

^aKey Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Gansu 730070, P. R. of China

^bKey Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Gansu 730070, P. R. of China eMail: wangxicun@nwnu.edu.cn

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Abstract

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Abstract

A metal-free synthesis of C2-functionalized pyrimidines via the reaction of pyrimidin-2-yl phosphates with amines and thiophenols in PEG-400 has been developed. The desired products can be generated in good to excellent yields in the environmentally friendly PEG-400, without any catalysts or other additives.

Key words

C2-functionalized pyrimidines - pyrimidin-2-yl phosphates - amines - thiophenols - cross-coupling - metal-free

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References

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19 We can obtain satisfactory results via the CuSO₄·5H₂O-catalyzed NaAsc-mediated cross-coupling of pyrimidin-2-yl phosphates 3 with amides 4. Using this method, we have successfully achieved the further functionalization of pyrimidin-2-yl phosphate 3k (Scheme 4).

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