Abstract
A trimethoxy derivative with three nonequivalent methoxy groups was obtained from 2,2′, 4-trichloro-6′-phenyl-4′ 5-dipyrimidinyl. Rearrangement of 2,2′, 4-trimethoxy-6′-phenyl-4′, 5-dipyrimidinyl under Hubert-Johnson conditions and thermal rearrangement with and without a catalyst make it possible to obtain 2′,4-dimethoxy-1-methyl-2-oxo-and 2′-methoxy-1,3-dimethy1-2,4-dioxodipyrimidinyls and both tri-N-methyl isomers, viz., the 1,1′, 3-and 1,3,3′-trimethyl derivatives. The possibility of obtaining N-methyl derivatives of trioxodipyrimidinyl by methylation under various conditions was also examined.
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M. A. Mikhaleva, I. I. Naumenko, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 6, 821 (1979).
J. Pliml and M. Prystas, Advances in Heterocyclic Chemistry, Vol. 8, Academic Press, New York-London (1967), p. 115.
G. E. Hardtman and F. G. Kathawala, Swiss Patent No. 539053 (1973); Chem. Abstr.,79, 115608 (1973).
D. J. Brown and T.-C. Lee, Austr. J. Chem.,21, 243 (1968).
D. J. Brown and T.-C. Lee, J. Chem. Soc., C, No. 1, 214 (1970).
D. J. Brown, The Pyrimidines, Suppl. I, Wiley Interscience, New York-London (1970), p. 276.
S.-H. Chang, J. Y. Koo, and Y. H. Kim, Korean Chem. Soc.,18, 210 (1974).
L. Strekowski, Pol. J. Chem.,52, 283 (1978).
The Sadtler Standard Spectra. NMR Spectra, Sadtler Research Laboratory, No. 5484.
The Sadtler Standard Spectra. NMR Spectra, Sadtler Research Laboratory, No. 12800.
M. A. Mikhaleva, V. V. Gulevich, I. I. Naumenko, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 5, 678 (1979).
T. Kato, N. Oda, and I. Ito, Chem. Pharm. Bull.,25, 215 (1977).
H. Schiff, Ann.,291, 367 (1896).
D. J. Brown, The Pyrimidines, Suppl. I, Wiley Interscience, New York-London (1970), p. 269.
W. F. Bryant and P. D. Klein, Anal. Biochem.,65, 73 (1975).
K. Yamauchi and M. Kinoshita, J. Chem. Soc., Perkin Trans. I, No. 4, 391 (1973).
A. Gordon and R. Ford, Chemist's Companion: A Handbook of Practical Data, Techniques, and References, Wiley (1973).
S. Senda, H. Kosaku, and J. Notani, Chem. Pharm. Bull.,20, 1380 (1972).
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See [1] for communication 70.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 398–403, March, 1980.
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Naumenko, I.I., Mikhaleva, M.A. & Mamaev, V.P. Pyrimidines. 71. Rearrangements of 2,2′,4-trimethoxy-6′-phenyl-4′,5-dipyrimidinyl to n-methyl oxo derivatives. Chem Heterocycl Compd 16, 303–308 (1980). https://doi.org/10.1007/BF02401733
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DOI: https://doi.org/10.1007/BF02401733