An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate

Tetrahedron

Volumn 65, Issue 4, 2009, Pages 757-764

  Morgentin, Rémy ^a   Jung, Frédéric ^a   Lamorlette, Maryannick ^a   Maudet, Mickaël ^a   Ménard, Morgan ^a   Plé, Patrick ^a   Pasquet, Georges ^a   Renaud, Fabrice ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Hydroxydeboronation; Nucleophilic substitution; Pyridine; Pyrimidine

Indexed keywords

2 (5 BROMO 3 METHOXYPYRIDIN 2 YL)ACETONITRILE; 2 CHLORO 3 METHOXY 5 NITROPYRIDINE; 3 BROMO 5 METHOXYPYRIDINE 1 OXIDE; 3 METHOXY 5 NITROPYRIDIN 2 OL; 3 METHOXY 5 NITROPYRIDIN2 OL; 5 BROMO 2 CHLORO 3 METHOXYPYRIDINE; 5 BROMO 2 CHLOROPYRIDIN 3 OL; 5 BROMOPYRIDIN 3 OL; [3 DIMETHYLAMINO 2 PHENYLMETHOXYPROP 2 ENYLIDENE]DIMETHYLAZANIUM HEXAFLUOROPHOSPHATE; ACETIC ACID DERIVATIVE; ETHYL 2 (5 HYDROXYPYRIMIDIN 2 YL)ACETATE; ETHYL 2 (5 PHENYLMETHOXYPYRIMIDIN 2 YL)ACETATE; ETHYL 2 AMINO 5 PHENYLMETHOXYPYRIDINE 3 CARBOXYLATE; ETHYL 3 AMINO 3 IMINOPROPANOATE HYDROCHLORIDE; METHYL 2 (3 METHOXY 5 NITROPYRIDIN 2 YL)ACETATE; METHYL 2 (5 AMINO 3 METHOXYPYRIDIN 2 YL)ACETATE; METHYL 2 (5 BROMO 3 METHOXYPYRIDIN 2 YL)ACETATE; METHYL 2 (5 BROMOPYRIMIDIN 2 YL)ACETATE; METHYL 2 (5 HYDROXY 3 METHOXYPYRIDIN 2 YL)ACETATE; METHYL 2 (5 HYDROXYPYRIMIDIN 2 YL)ACETATE; METHYL 2 BROMO 2 (5 BROMO 3 METHOXYPYRIDIN 2 YL)ACETATE; METHYL TERT BUTYL 2 (3 METHOXY 5 NITROPYRIDIN 2 YL)PROPANEDIOATE; PYRIDINE DERIVATIVE; TERT BUTYL 2 (5 BROMOPYRIMIDIN 2 YL)ACETATE; TERT BUTYL 2 (5 HYDROXYPYRIMIDIN 2 YL)ACETATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 57649106783     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.064     Document Type: Article

References (35)

1. Culkin D.A., and Hartwig J.F. Acc. Chem. Res. 36 (2003) 234-245
2. Hama T., and Hartwig J.F. Org. Lett. 10 (2008) 1549-1552
3. Golebiewski W.M., and Wrobel J.T. Bull. Pol. Acad. Sci. 38 (1990) 17-27
4. Spitzner D. Science of Synthesis Vol. 15 (2004), Georg Thieme, Stuttgart p 192
5. Liu M.-C., Lin T.-S., and Sartorelli A.C. Synth. Commun. 20 (1990) 2965-2970
6. Ablard J., Decoret C., Cronenberger L., and Pacheco H. Bull. Soc. Chim. Fr. 6 (1972) 2466-2481
7. Doktorova N.D., Ionova L.V., Karpeisky M.Y., Padyukova N.S., Turchin K.F., and Florentiev V.L. Tetrahedron 25 (1969) 3527-3553
8. Morisawa Y., Kataoka M., and Watanabe T. Chem. Pharm. Bull. 24 (1976) 1089-1093
9. Johnsen B.A., and Undheim K. Acta Chem. Scand. B37 (1983) 907-910
10. Iketmoto N., Miller R.A., Fleitz F.J., Liu J., Petrillo D.E., Leone J.F., Laquidara J., Marcune B., Karady S., Armstrong III J.D., and Volante R.P. Tetrahedron Lett. 46 (2005) 1867-1871
11. Comins D.L., and Killpack M.O. J. Org. Chem. 55 (1990) 69-73
12. Comins D.L., and Weglarz M.A. J. Org. Chem. 53 (1988) 4437-4442
13. Chapman, D. D.; Wu, E. U.S. Patent 4 204 870, 1980;
14. Mavunkel, B. J.; Perumattam, J. J.; Lu, Q.; Dugar, S.; Goyal, B.; Wang, D. X.; Chakravarty, S.; Luedtke, G. R.; Nashashibi, I.; Tester, R.; Tan, X. U.S. Patent 0 288 299, 2005.
15. Hanessian S., Saavedra O.M., Mascitti V., Marterer W., Oehrlein R., and Mak C.-P. Tetrahedron 57 (2001) 3267-3280
16. Wibaut J., and Zwart C. Recl. Trav. Chim. Pays-Bas 74 (1955) 1062-1069
17. Koch V., and Schnatterer S. Synthesis 6 (1990) 499-501
18. Talik T., Talik Z., and Ban-Oganowska H. Synthesis 4 (1974) 293-294
19. Hwan Lee S., Young Cho M., Hye Nam M., Sang Park Y., Woo Yoo B., Lee C.-W., and Min Yoon C. Synth. Commun. 35 (2005) 1335-1341
20. Voisin A., Bouillon A., Lancelot J., and Rault S. Tetrahedron (2005) 1417-1421
21. Kertesz, D. J.; Martin, M.; Palmer, W. S. U.S. Patent 0 234 236, 2005.
22. Coperet C., Adolfsson H., Khuong T.-A.V., Yudin A.K., and Sharpless K.B. J. Org. Chem. 63 (1998) 1740-1741
23. Tamura Y., Fujita M., Chen L.C., Kiyokawa H., Ueno K., and Kita Y. Heterocycles 15 (1981) 871-874
24. You J., and Verkade J.G. J. Org. Chem. 68 (2003) 8003-8007
25. Skerlj R.T., Bogucki D., and Bridger G.J. Synlett (2000) 1488-1490
26. Spitzner D. Science of Synthesis Vol. 15 (2004), Georg Thieme, Stuttgart p 169
27. Klapars A., Waldman J.H., Campos K.R., Jensen M.S., McLaughlin M., Chung J.Y.L., Cvetovich R.J., and Chen C.-Y. J. Org. Chem. 70 (2005) 10186-10189
28. Roth G.A., and McClymont E.L. J. Agric. Food Chem. 39 (1991) 612-616
29. Ragan J.A., McDermott R.E., Jones B.P., am Ende D.J., Clifford P.J., McHardy S.J., Heck S.D., Liras S., and Segelstein B.E. Synlett (2000) 1172-1174
30. Sakamoto T., Niitsuma S., Mizugaki M., and Yamanaka H. Heterocycles 8 (1977) 257
31. Jung, F. H.; Morgentin, R. R.; Plé, P. W.O. Patent 2007113548, 2007;
32. Jung, F. H.; Morgentin, R. R.; Plé, P. W.O. Patent 2007099323, 2007;
33. Jung, F. H.; Plé, P.; Pasquet G. R. W.O. Patent 2007113565, 2007;
34. Jung, F. H.; Plé, P. W.O. Patent 2007099335, 2007;
35. Jung, F. H.; Plé, P. W.O. Patent 2007099317, 2007.