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The need for transition metal catalysis to synthesize these nucleosides from pre\u2010functionalized building blocks and the use of nucleobase protection groups results in expensive and tedious syntheses. Herein we report that 5\u2010imidazolyl\u2010uracil can be obtained by scalable Van Leusen imidazole synthesis and regioselectively introduced on ribose to obtain the desired nucleoside in a 5 step synthesis (total yield 55\u2009%). The 5\u2010imidazolyl moiety leads to improved fluorescence properties. The only side\u2010product formed was characterized by 2D\u2010NMR and X\u2010ray crystallography and could be suppressed during synthesis in favor of the desired product.<\/jats:p>","DOI":"10.1002\/ejoc.202000563","type":"journal-article","created":{"date-parts":[[2020,5,27]],"date-time":"2020-05-27T09:01:08Z","timestamp":1590570068000},"page":"4022-4025","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["New Metal\u2010Free Route towards Imidazole\u2010Substituted Uridine"],"prefix":"10.1002","volume":"2020","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0043-2308","authenticated-orcid":false,"given":"Henri\u2010Philippe","family":"Mattelaer","sequence":"first","affiliation":[{"name":"Rega Institute for Medical Science Medicinal Chemistry KULeuven  Herestraat 49 3000 Leuven Belgium"},{"name":"Department of Chemistry, Molecular Design and Synthesis Leuven  Celestijnenlaan 200F 3001 Leuven Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4712-9376","authenticated-orcid":false,"given":"Anne\u2010Sophie","family":"Van Hool","sequence":"additional","affiliation":[{"name":"Rega Institute for Medical Science Medicinal Chemistry KULeuven  Herestraat 49 3000 Leuven Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3442-0316","authenticated-orcid":false,"given":"Flip","family":"de Jong","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Molecular Imaging and Photonics KULeuven  Celestijnenlaan 200F 3001 Leuven Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9022-1696","authenticated-orcid":false,"given":"Mark","family":"Van der Auweraer","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Molecular Imaging and Photonics KULeuven  Celestijnenlaan 200F 3001 Leuven Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2186-5209","authenticated-orcid":false,"given":"Luc","family":"Van Meervelt","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Biochemistry, Molecular and Structural Biology Section KULeuven  Celestijnenlaan 200F 3001 Leuven Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9597-0629","authenticated-orcid":false,"given":"Wim","family":"Dehaen","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Molecular Design and Synthesis Leuven  Celestijnenlaan 200F 3001 Leuven Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3589-8503","authenticated-orcid":false,"given":"Piet","family":"Herdewijn","sequence":"additional","affiliation":[{"name":"Rega Institute for Medical Science Medicinal Chemistry KULeuven  Herestraat 49 3000 Leuven Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,6,16]]},"reference":[{"key":"e_1_2_3_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd4010"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.6b00325"},{"key":"e_1_2_3_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrg1637"},{"key":"e_1_2_3_4_1","first-page":"1","volume":"26","author":"Seley\u2010Radtke K.","year":"2018","journal-title":"Antiviral Chem. 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