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Synthesis and structural studies of C-5 aryl- and C-6 alkyl-substituted pyrimidine derivatives

Abstract

C-5 and C-6 disubstituted pyrimidine derivatives 27 were synthesized. Introduction of the aryl rings at C-5 of pyrimidine moiety in 5 and 6 was performed using palladium-catalyzed Stille cross-coupling reaction. The novel C-6 fluorophenylalkylated 5-phenylpyrimidine derivative (7) was prepared by lithiation of 5-phenylpyrimidine (6) and subsequent reaction of thus obtained organolithium intermediate with p-fluoroacetophenone. The structures of 3, 4 and 6 were determined by X-ray crystal structure analysis. Both methoxy groups in these structures adopt a synperiplanar conformation with respect to the N1 and N3 atoms of the pyrimidine ring. The molecules of 3 and 4 are linked through weak Br···Br interactions into zig-zag chains. The molecules of 6 are assembled into layers by one C–H···O hydrogen bond, C–H···π and aromatic π···π stacking interactions.

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Acknowledgements

Support for this study was provided by the Ministry of Science of the Republic of Croatia (Projects #125-0982464-2925 and #119-1193079-3069).

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Correspondence to Silvana Raić-Malić.

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Gazivoda, T., Krištafor, S., Cetina, M. et al. Synthesis and structural studies of C-5 aryl- and C-6 alkyl-substituted pyrimidine derivatives. Struct Chem 19, 441–449 (2008). https://doi.org/10.1007/s11224-008-9302-2

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  • DOI: https://doi.org/10.1007/s11224-008-9302-2

Keywords

  • C-5 aryl pyrimidines
  • C-6 fluoroalkylated pyrimidines
  • Stille reaction
  • X-ray crystal structure analysis
  • Intermolecular interactions