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Synthesis and structure of novel pyrimidine‐thioethers: structural effects on reactivity along with an unpredicted dimethylamination reaction

2025-08-04Journal article Restricted access
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dc.contributor.authorCosta, Inês
dc.contributor.authorFrija, Luís M. T.
dc.contributor.authorAugusto, André
dc.contributor.authorPaixão, José A.
dc.contributor.authorCristiano, Maria de Lurdes
dc.date.accessioned2025-10-07T09:06:58Z
dc.date.available2025-10-07T09:06:58Z
dc.date.issued2025-08-04
dc.description.abstractBuchwald–Hartwig reactions have been in the spotlight over the past years due to their usefulness in creating a wide range of chemical skeletons applied in drug discovery. Aminopyrimidines are heterocyclic structures with significant biological relevance and compounds bearing the amino- and diaminopyrimidine motifs have been associated with antiviral, antibacterial, antiparasitic, antifungal, anticancer, and anti-inflammatory properties. Given the notable status of aminopyrimidines in the design of target-specific drug candidates, the synthesis and structure of four aminopyrimidine-arylsulfide conjugates (3, 4, 5, and 6) are reported that are designed to inhibit trypanothione reductase, a key enzyme in the redox pathway of trypanosomatids. When applying the Buchwald–Hartwig 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-protection of the starting 2,6-dichloropyrimidin-4-amine. The electron-withdrawing 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-based conjugates. The crystal structures of the novel aminopyrimidine-arylsulfide conjugate and their Boc-protected 2,6-dichloropyrimidin-4-amine precursors are disclosed and discussed.eng
dc.description.sponsorshipSFRH/BD/08242/2020
dc.identifier.doi10.1002/cphc.202500308
dc.identifier.eissn1439-7641
dc.identifier.issn1439-4235
dc.identifier.urihttp://hdl.handle.net/10400.1/27792
dc.language.isoeng
dc.peerreviewedyes
dc.publisherWiley
dc.relationAlgarve Centre for Marine Sciences
dc.relationAlgarve Centre for Marine Sciences
dc.relationCentre for Marine and Environmental Research
dc.relationCenter for Physics of the University of Coimbra
dc.relationCenter for Physics of the University of Coimbra
dc.relationCentro de Química Estrutural
dc.relationCentro de Química Estrutural
dc.relationInstitute of Molecular Sciences
dc.relationUIDB/04326/2020
dc.relation.ispartofChemPhysChem
dc.rights.uriN/A
dc.subjectBuchwald–Hartwing
dc.subjectCross-coupling reactions
dc.subjectDimethylamination
dc.subjectPyrimidine-thioethers
dc.subjectX-ray crystallography
dc.titleSynthesis and structure of novel pyrimidine‐thioethers: structural effects on reactivity along with an unpredicted dimethylamination reactioneng
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleAlgarve Centre for Marine Sciences
oaire.awardTitleAlgarve Centre for Marine Sciences
oaire.awardTitleCentre for Marine and Environmental Research
oaire.awardTitleCenter for Physics of the University of Coimbra
oaire.awardTitleCenter for Physics of the University of Coimbra
oaire.awardTitleCentro de Química Estrutural
oaire.awardTitleCentro de Química Estrutural
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oaire.citation.endPage11
oaire.citation.issue18
oaire.citation.startPage2
oaire.citation.titleChemPhysChem
oaire.citation.volume26
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oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85
person.familyNameCosta
person.familyNameAugusto
person.familyNameCristiano
person.givenNameInês
person.givenNameAndré
person.givenNameMaria de Lurdes
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0003-2711-5441
person.identifier.orcid0009-0001-7676-4774
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridG-2345-2012
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