Efficient synthesis of novel 6-substituted 2-(4-aryl-1,2,3-triazol-1-yl)pyrimidines and 7-deazapurines^*

* Dedicated to Professor Emeritus Povilas Vainilavicius on the occasion of his 75th birthday.

Abstract

A simple and efficient synthesis of 6-substituted 2-(4-aryl-1,2,3-triazol-1-yl)pyrimidines and 7-deazapurines from readily available 6-chloro-2-methylthiopyrimidine and 6-chloro-2-methylthio-7-deazapurine derivatives is described. The synthetic strategy is based on sequential reactions: substitution of 6-chlorine group with amines or (2-pyridyl)tributylstannane, oxidation of the obtained 6-substituted 2-methylthiopyrimidines, and 7-deazapurines to the corresponding 2-methylsulfonyl derivatives, their conversion to 2-azido derivatives and Cu(I)-catalyzed azide − alkyne cycloaddition reaction with arylethynes.

Graphical Abstract

Keywords:

• 1,2,3-triazoles
• 7-deazapurines
• Click chemistry
• pyrimidines
• Stille reaction

Acknowledgment

The research was funded by Lithuanian–Latvian–Chinese (Taiwanese) Tripartite Cooperation Programme No. [TAP-LLT-01/2015].