Abstract
An unequivocal synthesis of 5-chloro-7-methyl- (8) and 7-methyl-1,2,4-triazolo[1,5-a]pyrimidine (10) from 2-amino-4-chloro-6-methylpyrimidine (5) through the corresponding amidine6 and formamide oxime7 was developed. It was unambigously shown by comparison of the chemical shifts and the magnitude of coupling constants that the compounds obtained by condensation of 3-amino-1,2,4-triazole (12) and ethyl acetoacetate (13) and some further transformations are isomeric 5-methyl substituted 1,2,4-triazolo[1,5-a]pyrimidines1,9, and11.
Zusammenfassung
Es wurde ein eindeutiger Syntheseweg für 5-Chlor-7-methyl- (8) und 7-Methyl-1,2,4-triazolo[1,5-a]pyrimidin (10) ausgehend von 2-Amino-4-chlor-6-methylpyrimidin (5) über das entsprechende Amidin6 und das Formamidoxim7 entwickelt. Durch Vergleich von chemischen Verschiebungen und Kopplungskonstanten konnte eindeutig gezeigt werden, daß die Verbindungen, die bei der Kondensation von 3-Amino-1,2,4-triazol (12) and Ethylacetoacetat (13), sowie einige weitere Transformationsprodukte, isomere 5-Methylsubstituierte 1,2,4-Triazolo[1,5-a]pyrimidine sind (1,9,11).
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References
Büllow C, Haas K (1909) Ber 42: 4638
Birr E, Walther W (1953) Ber 86: 1401
Allen CFH, Beilfuss HR, Burness DM, Reynolds GA, Tinker JF, VanAllan JA (1959) J Org Chem 24: 787
Allen CFH, Beilfuss HR, Burness DH, Reynolds GA, Tinker JF, VanAllan JA (1959) J Org Chem 24: 779
Allen CFH, Beilfuss HR, Burness DM, Reynolds GA, Tinker JF, VanAllan JA (1959) J Org Chem 24: 796
Polanc S, Verček B, Šek B, Stanovnik B, Tišler M (1974) J Org Chem 39: 2143
Jenko B, Stanovnik B, Tišler M (1976) Synthesis 1976: 833
Verček B, Stanovnik B, Tišler M, Zrimšek Z (1978) Org Prep Proc Int 10: 239
Stanovnik B, Štimac A, Tišler M, Verček B (1982) J Heterocyclic Chem 19: 577
For a review see,Stanovnik B (1982) Chemicke Zvesti (Chemical Papers) 36: 693
Batterham TJ (1973) NMR Spectra of simple heterocycles. Wiley, New York, p 290
Ref 11,, p 291
Downing JW, Waluk JW, Stanovnik B, Tišler M, Verček B, Michl J (1985) J Org Chem 50: 302, and references cited therein
Shirikawa K (1958) Yakugaku Zasshi 78: 1395;Shirikawa K (1959) Chem Abstr 53: 8150 e
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Stanovnik, B., Urleb, U. & Tišler, M. An unequivocal synthesis of some substituted 1,2,4-triazolo[1,5-a]pyrimidines. Monatsh Chem 118, 601–606 (1987). https://doi.org/10.1007/BF00809671
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DOI: https://doi.org/10.1007/BF00809671