Two pathways toward 6-selanyl-2-triazolylpurine derivatives were designed. The first method involved the synthesisof 2-chloro-6-selanylpurine derivatives, further SNAr reaction with NaN3, and following CuAAC using different alkynes. The secondmethod was based on the synthesis of 2,6-bistriazolylpurine derivatives as starting materials followed by SNAr reaction withcommercial or in situ generated selenols as nucleophiles. A series of 2-chloro-6-selanylpurine derivatives were obtained in yields upto 84%. It was found that in the latter compounds, 6-selanyl moiety was the better leaving group compared to 2-chlorosubstituent inSNAr reactions. On the other hand, the SNAr reaction between 2,6-bistriazolylpurines and selenols or diselenides was successful, and13 examples of 6-selanyl-2-triazolylpurine derivatives were obtained in yields up to 87%. This direct approach for the Se−C bondformation proved the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as a good leaving group.