Diverse pyrimidine nucleoside analogues substituted at the 5-position of the heterocycle and their corresponding 2deoxyuridine series have shown a variety of interesting biological activities resulting in numerous active drugs that are used clinically such as antiviral agents.1,2 In addition, the C-5-aryl/heteroaryl nucleoside analogues have been utilised as fluorescent probes for detection of genetic material in cells3, as analytical tools in investigating RNA structure and function4, as biosensor for detection of carbohydrate-active enzyme glycosyltransferases5, and for the study of electron-transfer in an electrochemical DNA assay6. The binding motifs including sugar moiety (glycone) and nucleobase (aglycone) of these nucleoside derivatives are associated with a broad array of therapeutic importance in biological system. Among the nucleoside derivatives, introducing diversity into the aglycone moiety (base subunit, pyrimidine, uracil) represents promising strategies to improve binding affinity with target enzymes or to develop probes for sugar nucleoside utilising enzymes.7,8 For this perspective, a rapid access to a wide range of biologically active nucleosides a versatile approach to 5-substituted uridine analogues is required. This presentation discusses mild and practical reaction conditions for solid-phase SuzukiMiyaura cross coupling of 5-Iodouridine with various aryl/heteroaryl boronic acids, which can be extrapolated for the late stage modification of synthetically challenging uridine containing natural products, enzyme inhibitors or fluorescent biochemical probes.