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Synthesis 1998; 1998(1): 36-38
DOI: 10.1055/s-1998-1999
short paper
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Preparation of 4,6-Disubstituted 5-Pyrimidinesulfonamides

Wayne M. Best* , Marie-Anne M. Fam, Martin J. Gregory, Bruno Kasum, Philip L. Keep, Sam Lazzaro, Nicole Osner, Natasha Stewart, San H. Thang, Keith G. Watson
  • *ICI Australia, Research Group, Newsom St., Ascotvale, Victoria 3032, Australia; Fax + 61(3)99 05 45 97; E-mail: k.watson@sci.monash.edu.au
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Publikationsdatum:
31. Dezember 2000 (online)

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The first general synthesis of 4,6-disubstituted 5-pyrimidinesulfonamides is described. Treatment of 4,6-dichloro-5-benzylthiopyrimidine (3) with ethoxide or trifluoroethoxide, oxidation of the benzylthio group to a sulfonyl chloride and reaction with ammonia gave 4,6-dialkoxy-5-pyrimidinesulfonamides 5 a, b. Stepwise displacement of the trifluoroethoxy groups in 5 a gave a variety of symmetrical and non-symmetrical 4,6-disubstituted 5-pyrimidinesulfonamides 5 b - h.

pyrimidine - sulfonamides - trifluoroethoxy - substitution - nucleophilic