Synthesis and structural characterization of the C-6 fluoroalkylated pyrimidine derivatives

• Published in: Journal of molecular structure Vol. 923; no. 1; pp. 19 - 23
• Main Authors: Krištafor, Svjetlana, Gazivoda, Tatjana, Cetina, Mario, Makuc, Damjan, Plavec, Janez, Raić-Malić, Silvana
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 17.04.2009
• Subjects: C-6 fluoroalkylated pyrimidines; X-ray crystal structure analysis; π···π interactions; π···π interactions; X-ray crystal structure analysis; C-6 fluoroalkylated pyrimidines
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2008.12.037

C-6 substituted fluoroalkenyl 2,4-dimethoxypyrimidine derivative ( 4) was synthesized by lithiation of 2,4-dimethoxy-6-methylpyrimidine ( 3) and subsequent reaction of thus obtained organolithium intermediate with ethyl pentafluoropropionate. The novel 2,4-pyrimidinedione containing 3,3,4,4,4-pentafluoro-1-butenyl side chain ( 5) was prepared by demethoxylation of 4 using sodium iodide and chlorotrimethylsilane. The structures of 4 and 5 were confirmed by 1H, 13C and 19F NMR spectra, as well as IR spectra. The structure of 4 was also unambiguously confirmed by X-ray crystal structure analysis. The molecules of 4 are weakly linked by aromatic π···π stacking interactions into infinite chains parallel to the a axis.