Scale-up of the synthesis of a pyrimidine derivative directly on solid support

Organic Process Research and Development

Volumn 7, Issue 4, 2003, Pages 553-558

  Meisenbach, Mark ^a   Allmendinger, Thomas ^a   Mak, Ching Pong ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

4 (2 AMINO 6 PHENYLPYRIMIDIN 4 YL)BENZAMIDE; AMINOMETHYLPOLYSTYRENE; POLYSTYRENE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPARATIVE STUDY; SCALE UP; SOLID; SOLUTION AND SOLUBILITY; SYNTHESIS;

EID: 0042244423     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op034032t     Document Type: Article

References (19)

1. (a) Raillard, S. P.; Ji, G.; Mann, A. D.; Baer, T. A. Org. Process Res. Dev. 1999, 3, 177.
2. (b) Raillard, S. P.; Ji, G.; Mann, A. D.; Baer, T. A. U.S. Pat. Appl. Publ. U.S. 2002/028466, March 7, 2002.
3. Felder, E. R.; Marzinzik, A. L. J. Org. Chem. 1998, 63, 723.
4. Lee, S.; Robinson, G. Process Development: Fine Chemicals from Grams to Kilograms; Oxford University Press: Oxford, 1995.
5. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
6. Bernatowicz, M. S.; Daniels, S. B.; Köster, H. Tetrahedron Lett. 1989, 30, 4645.
7. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595.
8. Meienhofer, J.; Waki, M.; Heimer, E. P.; Lambros T. J.; Makofske R. C.; Chang, C. D. Int. J. Pep. Protein Res. 1979, 13, 35.
9. Yan, B.; Gremlich, H.-U.; Moss, S.; Coppola, G. M.; Sun, Q.; Liu, L. J. Comb. Chem. 1999, 1, 46.
10. Chiu, C.; Tang, Z.; Ellingboe, J. W. J. Comb. Chem. 1999, 1, 73.
11. Dyson, R. M.; Helg, A. G.; Meisenbach, M.; Allmendinger, T. 11th International Symposium on Pharmaceutical and Biomedical Analysis; Basle May 14-18 2000; P 007.
12. Frechet, J. M. J.; Haque K. E. Tetrahedron Lett. 1975, 16, 3055.
13. Adams, J. H.; Cook, R. M.; Hudson, D.; Jammalamadaka, V.; Lyttle, M. H.; Songster, M. F. J. Org. Chem. 1998, 63, 3706.
14. Zikos, C. C.; Ferderigos, N. G. Tetrahedron Lett. 1995, 36, 3741.
15. Edelstein, M.; Scott, P. E.; Sherlund, M.; Hansen, A. L.; Hughes, J. L. Chem. Eng. Sci. 1986, 41, 617.
16. Caciagli, V.; Cardinali, F.; Hansicke, A.; Tuchalski, G.; Lombardi, P. J. Pept. Sci. 1997, 3, 224.
17. These are made on request by AMSI-Glas AG, CH-4317 Wegenstetten, Switzerland.
18. Graffner-Nordberg, M.; Sjödin, K.; Tunek, A.; Hallberg, A. Chem. Pharm. Bull. 1998, 46, 591.
19. Aldol reaction of silylenol ethers with aldehydes catalysed with bismuth trichloride according to Ohki, H.; Wada, M.; Akiba, K. Tetrahedron Lett. 1988, 29, 4719.