Synthesis of 4-trifluoromethylpyrido[1,2-a]pyrimidin-2-ones utilizing activated alkynoates

Tetrahedron Letters

Volumn 44, Issue 18, 2003, Pages 3659-3662

  Harriman, Geraldine C B ^a   Chi, Shannon ^a   Zhang, Min ^a   Crowe, Andrea ^a   Bennett, Robert A ^a   Parsons, Ian ^a  

^a MILLENNIUM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 TRIFLUOROMETHYLPYRIDO[1,2 A]PYRIMIDIN 2 ONE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG SYNTHESIS;

EID: 0037471450     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00700-7     Document Type: Article

References (23)

1. Smith R.L., Barrett R.J., Sanders-Bush E. J. Pharmacol. Exp. Ther. 275:1995;1050-1057.
2. Awouters F., Vermeire J., Smeyers F., Vermote P., Van Beek R., Niemegeers C.J.E. Drug Dev. Res. 8:1986;95-102
3. Matsutani, S.; Mizushima, Y. Eur. Pat. Appl. 1989, EP 89-102635 19890216.
4. Yanagihara Y., Kasai H., Kawashima T., Shida T. Jpn. J. Pharmacol. 48:1988;91-101.
5. Hermecz I., Kokosi J., Podanyi B., Liko Z. Tetrahedron. 52:1996;7789.
6. Ferrarini P., Mori C., Mori F., Saccomanni G., Barontini S., Macchia M., Barili P., Hamdan M. J. Heterocyclic Chem. 36:1999;1076.
7. Ferrarini P., Mori C., Primofiore G., Calzolari L. J. Heterocyclic Chem. 27:1990;881.
8. Selic L., Strah S., Toplak R., Stanovnik B. Heterocycles. 47:1998;1017.
9. Selic L., Stanovnik B. J. Heterocyclic Chem. 34:1997;813.
10. Bowler A., Dinsmore A., Doyle P., Young D. J. Chem. Soc., Perkin Trans. 1. 9:1997;1297.
11. Prager R., Singh Y. Aust. J. Chem. 47:1994;1263.
12. Ye F., Chen B., Huang X. Synthesis. 4:1989;317.
13. Dorokhov V.A., Baranin S.V., Dib A., Bogdanov V.S., Yakovlev I.P., Stashina G.A., Zhulin V.M. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.). 39:1990;1918-1923.
14. Roma G., DiBraccio M.B., Albi A., Mazzei M., Ermili A. J. Heterocyclic Chem. 24:1987;329.
15. Doad G.J.S., Okor D.I., Scheinmann F., Bates P.A., Hursthouse M.B. J. Chem. Soc., Perkin Trans. 1. 1998;2993.
16. Acheson R.M., Wallis J.D. J. Chem. Soc., Perkin Trans. 1. 1982;1905.
17. Wilson J.G., Bottomley W. J. Heterocyclic Chem. 4:1967;360.
18. Adams R., Pachter I.J. J. Am. Chem. Soc. 74:1952;5491.
19. Yale H.L., Toeplitz B., Gougoutas J.Z., Puar M. J. Heterocyclic Chem. 10:1973;123.
20. 9.
21. Matsubara K., Oba Y., Usui Y. Magn. Reson. Chem. 36:1998;761-765.
22. CF=4.7 Hz), 18.2.
23. All compounds were characterized by NMR (Bruker AC 250 or 300 MHz instrument), LC/MS (Micromass platform LCZ with electrospray ionization and diode array LC detection at 200-400 nm), and CHN combustion analysis.