Synthesis and structural characterization of the C-6 fluoroalkylated pyrimidine derivatives
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-pentaf...
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Published in | Journal of molecular structure Vol. 923; no. 1; pp. 19 - 23 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
Elsevier B.V
17.04.2009
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Subjects | |
Online Access | Get full text |
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Summary: | 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. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-2860 1872-8014 |
DOI: | 10.1016/j.molstruc.2008.12.037 |