Pd-catalysed amidation of 2,6-dihalopurine nucleosides. Replacement of iodine at 0 °c

Tetrahedron Letters

Volumn 53, Issue 11, 2012, Pages 1358-1362

  Bosch, Lluís ^a   Cialîcu, Ionela ^a   Caner, Joaquim ^a   Ariza, Xavier ^a   Costa, Anna M ^a   Terrazas, Montserrat ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

2,6 Diaminopurine derivatives; C N bond formation; Pd insertions at 0 C

Indexed keywords

BENZAMIDE; BROMINE DERIVATIVE; CESIUM CARBONATE; CHLORINE; CHLORINE DERIVATIVE; IODINE; IODINE DERIVATIVE; METAL DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PALLADIUM; PALLADIUM COMPLEX; PALLADIUM DIBENZYLIDENEACETONE; PURINE NUCLEOSIDE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG; XANPTHOS;

AMIDATION; ARTICLE; ATOM; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CONTROLLED STUDY; DRUG SYNTHESIS; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 84856763306     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.01.012     Document Type: Article

References (80)

1. For recent reviews, see: D. Maiti, B.P. Fors, J.L. Henderson, Y. Nakamura, and S.L. Buchwald Chem. Sci. 2 2011 57 68
2. J.E.R. Sadig, and M.C. Willis Synthesis 2011 1 22 (synthesis of heterocycles)
3. D.S. Surry, and S.L. Buchwald Angew. Chem., Int. Ed 47 2008 6338 6361
4. J.F. Hartwig Acc. Chem. Res. 41 2008 1534 1544
5. I.J.S. Fairlamb Chem. Soc. Rev. 36 2007 1036 1045
6. S.L. Buchwald, C. Mauger, G. Mignani, and U. Scholz Adv. Synth. Catal. 348 2006 23 39
7. S. Schröter, C. Stock, and T. Bach Tetrahedron 61 2005 2245 2267
8. M.K. Lakshman Curr. Org. Synth. 2 2005 83 112
9. for very recent references on the Pd-catalysed amidations or aminations, see: M. Vimolratana, J.L. Simard, and S.P. Brown Tetrahedron Lett. 52 2011 1020 1022 (bidentate phosphines, 2-chloropyrimidine)
10. P.F. Thomson, P. Lagisetty, J. Balzarini, E. De Clercq, and M.K. Lakshman Adv. Synth. Catal. 352 2010 1728 1735 (Xantphos as the best ligand)
11. For a very recent review on purvalanol A, a cyclin-dependent kinase inhibitor, see: H.B. Tanowitz, and F.S. Machado Cancer Biol. Ther. 10 2010 326 328
12. for reviews on nelarabine (drug approved against T-cell acute lymphoblastic leukemia), see: A.M. Roecker, A. Stockert, and D.F. Kisor Clin. Med. Insights: Oncol. 4 2010 133 141
13. T. Robak, A. Korycka, E. Lech-Maranda, and P. Robak Molecules 14 2009 1183 1226
14. for entries to purine nucleosides and analogues with cytotoxic or cytostatic activity, see: R. Ottria, S. Casati, A. Manzocchi, E. Baldoli, M. Mariotti, J.A.M. Maier, and P. Ciuffreda Bioorg. Med. Chem. 18 2010 4249 4254
15. P. Naus, R. Pohl, I. Votruba, P. Dzubak, M. Hajduch, R. Ameral, G. Birkus, T. Wang, A.S. Ray, R. Mackman, T. Cihlar, and M. Hocek J. Med. Chem. 53 2010 460 470
16. also see the following review: M. Legraverend, and D.S. Grierson Bioorg. Med. Chem. 14 2006 3987 4006
17. For an entry to the subject, see the following reviews: E. Elzein, and J. Zablocki Expert Opin. Investig. Drugs 17 2008 1901 1910
18. D.K. Tosh, K.A. Jacobson, and L.S. Jeong Drugs Future 34 2009 43 52
19. X. Ariza, V. Bou, and J. Vilarrasa J. Am. Chem. Soc. 117 1995 3665 3673
20. M. Terrazas, X. Ariza, J. Farràs, J.M. Guisado-Yang, and J. Vilarrasa J. Org. Chem. 69 2004 5473 5475
21. M. Terrazas, X. Ariza, and J. Vilarrasa Tetrahedron Lett. 46 2005 5127 5130
22. M. Terrazas, X. Ariza, and J. Vilarrasa Org. Lett. 7 2005 2477 2479
23. J. Caner, and J. Vilarrasa J. Org. Chem. 75 2010 4880 4883
24. There are exceptions, however, depending on the nucleophile and medium. For an update, see: (a) Liu, J.; Robins, M. J. J. Am. Chem. Soc. 2007, 129, 5962-5968, and references cited therein;
25. 3, no substitution at C2 was observed; the chlorine atom of 6-chloro-2-cyano and 6-chloro-2-(benzylamino)carbonyl derivatives had been replaced by us under identical conditions (see: Bosch, L.; Vilarrasa, J. Tetrahedron Lett. 2011, 52, 753-756);
26. (c) in our hands, ammonia in anhydrous dioxane does not cleave the ester groups of the monosaccharide ring (see Robins, M. J.; Uznanski, B. Can. J. Chem. 1981, 59, 2608-2611, for related observations in DME); the amino-dechlorination reactions were almost quantitative.
27. S. Piguel, and M. Legraverend J. Org. Chem. 72 2007 7026 7029
28. also see: L. Vandromme, M. Legraverend, S. Kreimerman, O. Lozach, L. Meijer, and D.S. Grierson Bioorg. Med. Chem. 15 2007 130 141
29. X. Li, and R. Vince Bioorg. Med. Chem 14 2006 5742 5755
30. N. Ibrahim, and M. Legraverend J. Comb. Chem 11 2009 658 666 for other Pd-catalysed aminations and amidations of purines and purine nucleosides see Ref. 1
31. 2); see: P. Francom, and M.J. Robins J. Org. Chem. 68 2003 666 669
32. 2 and CuI in THF; see: A. Matsuda, M. Shinozaki, T. Yamaguchi, H. Homma, R. Nomoto, T. Miyasaka, Y. Watanabe, and T. Abiru J. Med. Chem. 35 1992 241 252
33. V. Nair, and S.G. Richardson Synthesis 1982 670 672
34. For a review, see: M.-N. Birkholz, Z. Freixa, and P.W.N.M. van Leeuwen Chem. Soc. Rev. 38 2009 1099 1118
35. 0 by heating with a small amount of water and a biarylphosphine, was very recently recommended for the coupling of aryl chlorides with carboxamides or ureas. See: B.P. Fors, P. Krattiger, E. Strieter, and S.L. Buchwald Org. Lett. 10 2008 3505 3508
36. B.P. Fors, K. Dooleweert, Q. Zeng, and S.L. Buchwald Tetrahedron 65 2009 6576 6583
37. S. Breitler, N.J. Oldenhuis, B.P. Fors, and S.L. Buchwald Org. Lett 13 2011 3262 3265
38. [Pd(dba)Xantphos] may be the predominant species according to studies on the nature of bidentate phosphine-Pd complexes: C. Amatore, G. Broeker, A. Jutand, and F. Khalil J. Am. Chem. Soc. 119 1997 5176 5185
39. L.M. Klingensmith, E.R. Strieter, T.E. Barder, and S.L. Buchwald Organometallics 25 2006 82 91
40. There are several examples, however, of efficient Kumada-Corriu couplings (RMgX, ArX, Pd) even below 0 °C: V. Bonnet, F. Mongin, F. Trécourt, G. Quéguiner, and P. Knochel Tetrahedron Lett. 42 2001 5717 5720
41. V. Bonnet, F. Mongin, F. Trécourt, G. Quéguiner, and P. Knochel Tetrahedron 58 2002 4429 4438
42. M.G. Organ, M. Abdel-Hadi, S. Avola, N. Hadei, J. Nasielski, C.J. O'Brien, and C. Valente Chem. Eur. J. 13 2007 150 157
43. R. Martin, and S.L. Buchwald J. Am. Chem. Soc. 129 2007 3844 3845 there is one example (ArCl, morpholine, LiHMDS, SPhos-Pd0,-10 °C, DME) of amination below rt
44. M.R. Biscoe, B.P. Fors, and S.L. Buchwald J. Am. Chem. Soc. 130 2008 6686 6687
45. for Negishi reactions below rt, see: J. Liu, Y. Deng, H. Wang, H. Zhang, G. Yu, B. Wu, H. Zhang, Q. Li, T.B. Marder, Z. Yang, and A. Lei Org. Lett. 10 2008 2661 2664
46. S. Wunderlich, and P. Knochel Chem. Commun. 2008 6387
47. J. Liu, H. Wang, H. Zhang, X. Wu, H. Zhang, Y. Deng, Z. Yang, and A. Lei Chem. Eur. J. 15 2009 4437 4445
48. T. Thaler, B. Haag, A. Gavryushin, K. Schober, E. Hartmann, R.M. Gschwind, H. Zipse, P. Mayer, and P. Knochel Nature Chem. 2 2010 125 130
49. S. alimsiz, M. Sayah, D. Mallik, and M.G. Organ Angew. Chem., Int. Ed. 49 2010 2014 2017
50. for a Suzuki coupling below rt, see: X. Urbaneja, A. Mercier, C. Besnard, and E.P. Kündig Chem. Commun. 47 2011 3739 3741
51. for a Sonogashira reaction, see: K. Nakamura, H. Okubo, and M. Yamaguchi Synlett 1999 549 550
52. We prepared 7 from 3 and benzyl alcohol and NaH at rt, that is, via a SNAr-like reaction, while 8 was prepared according to the procedure of Gundersen et al. for the analogous benzyl derivative: G. Langli, L.-L. Gundersen, and F. Rise Tetrahedron 52 1996 5625 5638
53. 2), and references therein
54. 2)
55. M.L.H. Mantel, A.T. Lindhardt, D. Lupp, and T. Skrydstrup Chem. Eur. J. 16 2010 5437 5442 (tosylates, oxazolidin-2-one)
56. J.D. Hicks, A.M. Hyde, A. Martínez-Cuezva, and S.L. Buchwald J. Am. Chem. Soc. 131 2009 16720 16734 (N-subst. carbamates & sulfonamides)
57. tBuXPhos preferred, rt)
58. A.A. Trabanco, J.A. Vega, and M.A. Fernández J. Org. Chem. 72 2007 8146 8148 (fluorinated carbamates)
59. II, Xantphos preferred, carbamates & sulfonamides)
60. K. Fujita, M. Yamashita, F. Puschmann, M.M. Alvarez-Falcon, C.D. Incarvito, and J.F. Hartwig J. Am. Chem. Soc 128 2006 9044 9045 (Xantphos, 2-oxazolidinone and TsNHMe)
61. J. Yin, and S.L. Buchwald Org. Lett 2 2000 1101 1104
62. J. Yin, and S.L. Buchwald J. Am. Chem. Soc 124 2002 6043 6048
63. G. Burton, P. Cao, G. Li, and R. Rivero Org. Lett 5 2003 4373 4376
64. D. Steinhuebel, M. Palucki, D. Askin, and U. Dolling Tetrahedron Lett. 45 2004 3305 3307 (sultams)
65. M. Carril, R. SanMartín, E. Domínguez, and I. Tellitu Tetrahedron 63 2007 690 702
66. T. Ikawa, T.E. Barder, M.R. Biscoe, and S.L. Buchwald J. Am. Chem. Soc 129 2007 13001 13007
67. J. Porter, S. Lumb, F. Lecomte, J. Reuberson, A. Foley, M. Calmiano, K. le Riche, H. Edwards, J. Delgado, R.J. Franklin, J.M. Gascon-Simorte, A. Maloney, C. Meier, and M. Batchelor Bioorg. Med. Chem. Lett. 19 2009 397 400
68. B.A. Johns, J.G. Weatherhead, S.H. Allen, J.B. Thompson, E.P. Garvey, S.A. Foster, J.L. Jeffrey, and W.H. Miller Bioorg. Med. Chem. Lett. 19 2009 1807 1810
69. F. Micheli, G. Bonanomi, R. Di Fabio, G. Gentile, L. Tarsi, S. Terreni, D. Hamprecht, D. Donati, C. Heidbreder, and A. Prandi Bioorg. Med. Chem. Lett. 20 2010 5491 5494
70. R.S. Shetty, Y. Lee, B. Liu, A. Husain, R.W. Joseph, Y. Lu, D. Nelson, J. Mihelcic, W. Chao, K.K. Moffett, A. Schumacher, D. Flubacher, A. Stojanovic, M. Bukhtiyarova, K. Williams, K.-J. Lee, A.R. Ochman, M.S. Saporito, W.R. Moore, G.A. Flynn, B.D. Dorsey, E.B. Springman, T. Fujimoto, and M.J. Kelly J. Med. Chem. 54 2011 179 200
71. B. Liu, R.S. Shetty, K.K. Moffett, and M.J. Kelly Tetrahedron Lett. 52 2011 1680 1684
72. B.R. Rosen, J.C. Ruble, T.J. Beauchamp, and A. Navarro Org. Lett. 13 2011 2564 2567
73. S. Shekhar, T.B. Dunn, B.J. Kotecki, D.K. Montavon, and S.C. Cullen J. Org. Chem. 76 2011 4552 4563 Also see Refs. 16d and 16g
74. T. Fukuyama, C.-K. Jow, and M. Cheung Tetrahedron Lett. 36 1995 6373 6374
75. Y. Hidai, T. Kan, and T. Fukuyama Tetrahedron Lett. 40 1999 4711 4714
76. T. Kan, and T. Fukuyama Chem. Commun. 2004 353 359
77. Y. Aihara, A. Yoshida, T. Furuta, T. Wakimoto, T. Akizawa, M. Konishi, and T. Kan Bioorg. Med. Chem. Lett. 19 2009 4171 4174 Also see Ref. 4c
78. A one-pot trial from 2, adding first the carboxamide and then the carbamate gave a similar outcome. For sequential replacements of two halogens via Suzuki reactions, with parallel results, see: I. Čerňa, R. Pohl, B. Klepetářová, and M. Hocek J. Org. Chem. 73 2008 9048 9054
79. I. Čerňa, R. Pohl, B. Klepetářová, and M. Hocek Org. Lett. 8 2006 5389 5392
80. M. Havelková, D. Dvořák, and M. Hocek Synthesis 2001 1704 1710