A highly facile and efficient one-step synthesis of N6-adenosine and N6-2′-deoxyadenosine derivatives

Organic Letters

Volumn 7, Issue 26, 2005, Pages 5877-5880

  Wan, Zhao Kui ^a   Binnun, Eva ^a   Wilson, Douglas P ^a   Lee, Jinbo ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE; DEOXYADENOSINE DERIVATIVE; DRUG DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ADENOSINE; COMBINATORIAL CHEMISTRY TECHNIQUES; DEOXYADENOSINES; MOLECULAR STRUCTURE;

EID: 30144441430     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052424+     Document Type: Article

References (37)

1. Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley: New York, 1979.
2. For representative references, see: (a) Srivastava, P. C.; Robins, R. K.; Meyer, R. B., Jr. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum: New York, 1988; Vol. 1, pp 113-281.
3. (b) Liu, J.; Janeba, Z.; Robins, M. J. Org. Lett. 2004, 6, 2917-2920.
4. (c) Han, S.; Harris, C. M.; Harris, T. M.; Kim, H.-Y. H.; Kim, S. J. J. Org. Chem. 1996, 61, 174.
5. (d) Nair, V.; Richardson, S. G. J. Org. Chem. 1980, 45, 3969.
6. (e) Véliz, E. A.; Beal, P. A. Tetrahedron Lett. 2000, 41, 1695-1697.
7. (f) Véliz, E. A.; Beal, P. A. J. Org. Chem. 2001, 66, 8592 and references therein.
8. For recent reviews, see: (g) Lakshman, M. K. J. Organomet. Chem. 2002, 653, 234-251.
9. (h) Hocek, M. Eur. J. Org. Chem. 2003, 245-254.
10. Robins, M. J.; Basom, G. L. Can. J. Chem. 1973, 51, 3161-3169.
11. (a) Maruenda, H.; Chenna, A.; Liem, L.-K.; Singer, B. J. Org. Chem. 1998, 63, 4385-4389.
12. (b) Lakshman, M. K.; Keeler, J. C.; Hilmer, J. H.; Martin, J. Q. J. Am. Chem. Soc. 1999, 121, 6090-6091.
13. (c) Lakshman, M. K.; Sayer, J. M.; Jerina, D. M. J. Am. Chem. Soc. 1991, 113, 6589-6594.
14. (d) Lakshman, M. K.; Lehr, R. E. Tetrahedron Lett. 1990, 31, 1547-1550.
15. (e) Kim, S. J.; Harris, C. M.; Jung, K.-Y.; Koreeda, M.; Harris, T. M. Tetrahedron Lett. 1991, 32, 6073-6076.
16. Lakshman, M. K.; Keeler, J. C.; Hilmer, J. H.; Martin, J. Q. J. Am. Chem. Soc. 1999, 121, 6090-6091.
17. De Riccardis, F.; Bonala, R. R.; Johnson, F. J. Am. Chem. Soc. 1999, 121, 10453-10460.
18. Elmquist, C. E.; Stover, J. S.; Wang, Z.; Rizzo, C. J. J. Am. Chem. Soc. 2004, 126, 11190-111201.
19. (a) Dai, Q.; Ran, C.; Harvey, R. G. Org. Lett. 2005, 7, 999-1002.
20. (b) Lee, H.; Luna, E.; Hinz, M.; Stezowski, J. J.; Kiselyov, A. S.; Harvey, R. G. J. Org. Chem. 1995, 60, 5604-5613.
21. (a) Castro, B.; Dormoy, J. R.; Evin, C. Tetrahedron Lett. 1975, 14, 1219-1222.
22. (b) Campagne, J.-M.; Coste, J.; Jouin, P. J. Org. Chem. 1995, 60, 5214-5223 and references therein.
23. Wan, Z.-K. Unpublished results.
24. Lin, X.; Robins, M. J. Org. Lett. 2000, 2, 3497-3499.
25. Appel, R. Angew. Chem., Int. Ed. Engl. 1975, 14, 801-811.
26. Sung, W. L. J. Org. Chem. 1982, 47, 3623-3628.
27. Mansour, T. S.; Evans, C. A.; Siddiqui, M. A.; Charron, M.; Zacharie, B.; Nguyen-Ba, N.; Lee, N.; Korba, B. Nucleosides Nucleotides 1997, 16, 993-1001.
28. Phosphonium salts of primary and secondary alcohols readily undergo nucleophilic substitutions. (a) Castro, B.; Chapleur, Y.; Gross, B.; Selve, C. Tetrahedron Lett. 1972, 5001-5004.
29. (b) Castro, B.; Selve, C. Tetrahedron Lett. 1973, 4459-4463.
30. (c) Downie, I. M.; Heaney, H.; Kemp, G. Tetrahedron 1988, 44, 2619-2624 and references therein.
31. PyBOP and PyBroP were also active towards activation of inosine but less effective. DMF was found to be the best solvent.
32. The phosphonium salt was observed on LCMS.
33. Representative Procedure. To a solution of (-)-inosine (268 mg, 1.0 mmol) and BOP (530.7 mg, 1.2 mmol) in DMF (5 mL) was added DIPEA (0.261 mL, 1.5 mmol), followed by addition of benzylamine (0.131 mL, 1.2 mmol) at room temperature under the nitrogen. The reaction mixture was stirred overnight (∼16 h) at room temperature. The solvent was removed under vacuum, and the crude product was purified on a silica gel column eluted with 0-15% MeOH in DCM to give the desired product 9a as a white solid (355 mg, 99+%). All products in both Table 1 and Table 2 have been fully characterized.
34. Mechanistic studies are underway. For work on BtH, see: Katritzky, R. A.; Manju, K.; Singh, S. K.; Meher, N. K. Tetrahedron 2005, 61, 2555-2581 and references therein.
35. Seela, F.; Herdering, W.; Kehne, A. Helv. Chim. Acta 1987, 70, 1649-1660.
36. (a) Harvey, R. G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, England, 1991.
37. (b) Glatt, H.; Seidel, A.; Harvey, R. G.; Coughtrie, M. W. H. Mutagenesis 1994, 9, 553-557.