Synthetic methodologies towards different types of novel 2- and 6-alkyl/arylthiopurine nucleosides, including those containing 1,2,3-triazolyl moieties are described. The title compounds were obtained by SNAr reactions between 2,6-diazido-, 2,6-dichloro- and 2,6-bistriazolylpurine nucleosides and different S-nucleophiles. The chemical reactivity of the aforementioned variously substituted purine nucleosides towards different S-nucleophiles is discussed. The obtained monoazido purine nucleoside intermediates exist in azide and tetrazole tautomeric forms. These compounds were later used in 1,3-dipolar cycloaddition reactions with different terminal alkynes. The obtained sulfur-containing nucleoside analogs are interesting in terms of medicinal chemistry.