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Aminopyrimidines are heterocyclic structures with significant biological relevance and compounds bearing the amino\u2010 and diaminopyrimidine motifs have been associated with antiviral, antibacterial, antiparasitic, antifungal, anticancer, and anti\u2010inflammatory properties. Given the notable status of aminopyrimidines in the design of target\u2010specific drug candidates, the synthesis and structure of four aminopyrimidine\u2010arylsulfide conjugates (<jats:bold>3<\/jats:bold>, <jats:bold>4<\/jats:bold>, <jats:bold>5<\/jats:bold>, and <jats:bold>6<\/jats:bold>) are reported that are designed to inhibit trypanothione reductase, a key enzyme in the redox pathway of trypanosomatids. When applying the Buchwald\u2013Hartwig synthetic approach, the formation of different products is witnessed by altering the reaction conditions, observing that regioselectivity is conditioned by reaction time and by Boc\u2010protection of the starting 2,6\u2010dichloropyrimidin\u20104\u2010amine. The electron\u2010withdrawing character of the protecting group appears to increase the susceptibility of the pyrimidine at C2 for further reaction with the solvent, DMF, yielding the corresponding diaminopyrimidine\u2010based conjugates. The crystal structures of the novel aminopyrimidine\u2010arylsulfide conjugate and their Boc\u2010protected 2,6\u2010dichloropyrimidin\u20104\u2010amine precursors are disclosed and discussed.<\/jats:p>","DOI":"10.1002\/cphc.202500308","type":"journal-article","created":{"date-parts":[[2025,8,4]],"date-time":"2025-08-04T21:34:01Z","timestamp":1754343241000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and Structure of Novel Pyrimidine\u2010Thioethers: Structural Effects on Reactivity along with an Unpredicted Dimethylamination Reaction"],"prefix":"10.1002","volume":"26","author":[{"given":"In\u00eas C. 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