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Synthesis 2015; 47(24): 3925-3935
DOI: 10.1055/s-0035-1560175
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
Further Information
Publication History
Received: 03 July 2015
Accepted after revision: 23 July 2015
Publication Date:
02 September 2015 (online)
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-freeSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560175.
- Supporting Information
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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).