An eco-efficient pilot plant scale synthesis of two 5-substituted-6,7- dimethoxy-1-H-quinazoline-2,4-diones

Green Chemistry

Volumn 7, Issue 8, 2005, Pages 586-589

  Connolly, Terrence J ^a   McGarry, Patrick ^a   Sukhtankar, Sunil ^a  

^a ROCHE BIOSCIENCE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23844442559     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b504305k     Document Type: Article

References (38)

1. D. J. C. Constable, A. D. Curzons, L. M. Freitas dos Santos, G. R. Geen, R. E. Hannah, J. D. Hayler, J. Kitteringham, M. A. McGuire, J. E. Richardson, P. Smith, R. L. Webb and M. Yu, Green Chem., 2001, 3, 7-9.
2. D. J. C. Constable, A. D. Curzons and V. L. Cunningham, Green Chem., 2002, 4, 521-527.
3. A. D. Curzons, D. J. C. Constable, D. N. Mortimer and V. L. Cunningham, Green Chem., 2001, 3, 1-6.
4. J. F. Jenck, F. Agterberg and M. J. Droescher, Green Chem., 2004, 6, 544-556.
5. J.-P. Lange, Green Chem., 2002, 4, 546-550.
6. Information regarding Roche's commitment to sustainability is available on our website at http://www.roche.com/home/sustainability.htm.
7. P. J. Dunn, S. Galvin and K. Hettenbach, Green Chem., 2004, 6, 43-48.
8. T. J. Connolly, P. F. Keitz, E. K. Lee, J. Li, F. J. Lopez-Tapia, P. F. McGarry, C. R. Melville, D. Nitzan, C. O'Yang, F. Padilla and K. K. Weinhardt, WO2005005395, 2005.
9. T. J. Connolly, M. Matchett and K. Sarma, Org. Process Res. Dev., 2005, 9, 80-87.
10. T. Mizuno, N. Okamoto, T. Ito and T. Miyata, Tetrahedron Lett., 2000, 41, 1051-1053.
11. T. Mizuno and Y. Ishino, Tetrahedron, 2002, 58, 3155-3158.
12. A. Bassoli, B. Rindone, S. Tollari and F. Chioccara, J. Mol. Catal., 1990, 60, 41-48.
13. T. Miyata, T. Mizuno, Y. Nagahama, I. Nishiguchi, T. Hirashima and N. Sonoda, Heteroat. Chem, 1991, 2, 473-475.
14. S. W. Schneller, A. C. Ibay, W. J. Christ and R. F. Bruns, J. Med. Chem., 1989, 32, 2247-2254.
15. E. B. Skibo, J. Org. Chem., 1985, 50, 4861-4865.
16. M. A. Alkhader, R. C. Perera, R. P. Sinha and R. K. Smalley, J. Chem. Soc., Perkin Trans. 1, 1979, 1056-1062.
17. D. W. Combs and M. S. Rampulla, J. Heterocycl. Chem., 1989, 26, 1885-1886.
18. J. DeRuiter, A. N. Brubaker, J. Millen and T. N. Riley, J. Med. Chem., 1986, 29, 627-629.
19. P. D. Hammen and D. J. M. Allen, J. Heterocycl. Chem., 1987, 24, 1701-1703.
20. M. C. Venuti, R. A. Stephenson, R. Alvarez, J. J. Bruno and A. M. Strosberg, J. Med. Chem., 1988, 31, 2136-2145.
21. N. A. Lange and F. E. Sheibley, Org. Synth. Coll., Vol. II, 1943, 79-80 and references cited therein.
22. E. H. Huntress and J. V. K. Gladding, J. Am. Chem. Soc., 1942, 64, 2644-2649.
23. G. H. Jones, M. C. Venuti, R. Alvarez, J. J. Bruno, A. H. Berks and A. Prince, J. Med. Chem., 1987, 30, 295-303.
24. S. Goto, H. Tsuboi, M. Kanoda, K. Mukai and K. Kagara, Org. Process Res. Dev., 2003, 7, 700-706.
25. B. A. Kowalczyk, P. N. Roberts, G. K. McEwen and J. Robinson, III, Org. Process Res. Dev., 1997, 1, 355-358.
26. 2,3,4-Trimethoxybenzoic acid is commercially available from many vendors.
27. T. J. Connolly, M. Matchett, P. McGarry, S. Sukhtankar and J. Zhu, Org. Process Res. Dev., 2004, 8, 624-627.
28. P. A. Grieco, Organic Synthesis in Water, Blackie Academic and Professional, London, 1998.
29. C.-J. Li and T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley and Sons, New York, 1997.
30. Bretherick's Handbook of Reactive Chemical Hazards, Butterworth- Heinemann, Boston, 5th edn., 1995, vol. 1, 1506-1511.
31. Bretherick's Handbook of Reactive Chemical Hazards, Butterworth- Heinemann, Boston, 5th edn., 1995, vol. 2, 168-169.
32. S. H. Merrill, J. Org. Chem., 1960, 25, 1882-1883.
33. Solka-floc is a powered cellulose filter aid.
34. Although it is theoretically possible to recycle the catalyst by recovering it from the filter cake, this is not practical in our facility because of quality and safety issues. Catalysts are recycled indirectly by returning the filter cakes that contain the spent catalyst to the metal refiner, where the metal is extracted and converted into fresh batches of catalyst.
35. In the Palo Alto pilot plant, hydrogenations performed at 5 psi above atmospheric pressure do not require specialized equipment.
36. N. G. Anderson, Practical Process Research & Development, Academic Press, San Diego, CA, 2000, p. 16.
37. R. A. Sheldon, Chem. Ind., 1992, 903-906.
38. R. A. Sheldon, Chem. Ind., 1997, 12-15.