A novel practical synthesis of C-2-arylpurines

Advanced Synthesis and Catalysis

Volumn 346, Issue 13-15, 2004, Pages 1859-1867

  Itoh, Takahiro ^a   Sato, Kimihiko ^a   Mase, Toshiaki ^a  

^a Banyu Pharmaceutical   (Japan)

Author keywords

Metallocenes; P ligands; Palladium; Purine; Pyrimidine; Suzuki Miyaura cross coupling

Indexed keywords

2 PHENYL 8 METHYLPURINE; 2 PHENYLPURINE; 2,8 DIPHENYLPURINE; 8 AMINOPHENYL 2 PHENYLPURINE; 8 HYDROXY 2 PHENYLPURINE; 8 MERCAPTO 2 PHENYLPURINE; BORONIC ACID DERIVATIVE; DIAMINE; FERROCENE DERIVATIVE; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; HYDROLYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 12344314099     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404159     Document Type: Article

References (91)

1. a) H. Haning, U. Niewöhner, T. Schenke, M. Es-Sayed, G, Schmidt, T. Lampe, E. Bischoff, Bioorg. Med. Chem. Lett. 2002, 12, 865-868;
2. b) J. C. Morales, E. T. Kool, J. Am. Chem. Soc. 1999, 121, 2323-2324;
3. c) E. T. Kool, J. C. Morales, K. M. Guckian, Angew. Chem. Int. Ed. 2000, 39, 990-1009;
4. d) J. C. Morales, E. T. Kool, J. Am. Chem. Soc. 2000, 122, 1001-1007;
5. e) C. L. Chepanoske, C. R. Langelier, N. H. Chmiel, S. S. David, Org. Lett. 2000, 2, 1341-1344;
6. f) E. D. Clercq, J. Med. Chem. 1986, 29, 1561-1569;
7. g) C. G. Wong, R. B. Jr. Meyer, J. Med. Chem. 1984, 27, 429-432;
8. h) A. K. Bakkestuen, L. L. Gundersen, G. Langli, F. Liu, J. M. J. Nolsøe, Bioorg. Med. Chem. Lett. 2000, 10, 1207-1210.
9. A. Murata, K. Masumoto, M. Kondo, K. Furukawa, M. Oka, Japanese Patents JP 2002167387, JP 2001048882 A2, JP 20010220.
10. K. Hirota, K. Kazaoka, I. Niimoto, H. Kumihara, H. Sajiki, Y. Isobe, H. Takaku, M. Tobe, H. Ogita, T. Ogino, S. Ichii, A. Kurimoto, H. Kawakami, J. Med. Chem. 2002, 45, 5419-5422.
11. J.-J. Bourguignon, L. Désaubry, P. Raboisson, C.-G. Wermuth, C. Lugnier, J. Med. Chem. 1997, 40, 1768-1770.
12. Y. Maki, Y. Fujioka, S. Oohara, C. Kin, Japanese Patent JP 08165292 A2, JP 19960625, 1996.
13. E. Chapman, S. Ding, P. G. Schultz, C-H. Wong, J. Am. Chem. Soc. 2002, 124, 14524-14525.
14. A. M. Bianucci, G. Biagi, A. Coi, I. Giorgi, L. Oreste, F. Pacchini, V. Scartoni, A. Lucacchini, B. Costa, Drug Dev. Res. 2001, 54, 52-65.
15. a) G. Biagi, I. Giorgi, O. Livi, F. Pacchini, P. Rum, V. Scartoni, B. Costa, M. R. Mazzoni, L. Giusti, Farmaco 2002, 57. 221-233;
16. b) G. Bojack, C. G. Earnshaw, R. Klein, S. D. Lindell, C. Lowinski, R. Preuss, Org. Lett. 2001, 3, 839-842;
17. c) T. Yamada, Japanese Patent JP 07118288 A2 19950509, 1995;
18. d) G. Biagi, I. Giorgi, L. Oreste, S. Valerio, Farmaco 1992, 47, 537-550.
19. a) T. J. J. Muller, R. Braun, M. Ansorge, Org. Lett. 2000, 2, 1967-1970;
20. b) E. C. Taylor, O. Vogl, C. C. Cheng, J. Am. Chem. Soc. 1959, 81, 2442-2448;
21. c) R. M. Dodson, J. K. Seyler, J. Org. Chem. 1951, 16, 461-465;
22. d) B. L. Booth, A. M. Dias, M. F. Proença, M. E. A. Zaki, J. Org. Chem. 2001, 66, 8436-8441;
23. e) R. B. Jr. Meyer, D. A. Shuman, R. K. Robins, J. Am. Chem. Soc. 1974, 96, 4962-4966.
24. a) V. Nair, D. A. Young, R. Jr. DeSilvia, J. Org. Chem. 1987, 52, 1344-1347;
25. b) V. Nair, D. A. Young, J. Org. Chem. 1984, 49, 4340-4344;
26. c) V. Nair, S. G. Richardson, R. E. Coffman, J. Org. Chem. 1982. 47, 4520-4524.
27. A. Matsuda, K. Satoh, H. Tanaka, T. Miyasaka, Synthesis 1984, 963-965.
28. a) V. Bonnet, F. Mongin, F. Trécourt, G. Quéguiner, P. Knochel, Tetrahedron 2002, 58, 4429-4438;
29. b) N. M. Simkovsky, M. Ermann, S. M. Roberts, D. M. Parry, A. D. Baxter, J. Chem. Soc. Perkin Trans. 1 2002, 1847-1849.
30. a) V. Nair, G. A. Turner, S. D. Chamberlain, J. Am. Chem. Soc. 1987, 109, 7223-7224;
31. b) V. Nair, G. A. Turner, S. D. Buenger, S. D. Chamberlain, J. Org. Chem. 1988, 53, 3051-3057;
32. c) L. L. Gundersen, A. K. Bakkestuen, A. J. Aasen, H. Øversa, F. Rise, Tetrahedron 1994, 50, 9 743-9756;
33. d) L. L. Gundersen, Tetrahedron Lett. 1994, 35, 3155-3158;
34. e) G. Langli, L. L. Gundersen, F. Rise, Tetrahedron 1996, 52, 5625-5638;
35. f) V. Nair, G. S. Buenger, J. Am. Chem. Soc. 1989, 111, 8502-8504;
36. g) V. Nair, D. F. Purdy, T. B. Sells, J. Chem. Soc. Chem. Commun. 1989, 878-879;
37. h) V. Nair, D. F. Purdy, Tetrahedron 1991, 47, 365-382.
38. a) K. Hirota, Y. Kitade, Y. Kanbe, Y. Maki, J. Org. Chem. 1992, 57, 5268-5270;
39. b) A. Holy, J. Günter, H. Dvořáková, M. Masojídková, G. Andrei, R. Snoeck, J. Balzarini, E. De Clercq, J. Med. Chem. 1999, 42, 2064-2086;
40. c) M. Česnek, M. Hocek, A. Holý, Collect. Czech. Chem. Commun. 2000, 65, 1357-1373;
41. d) M. Hocek, A. Holý, H. Dvořáková, Collect. Czech. Chem. Commun. 2002, 67, 325-335;
42. e) H. Dvořáková, D. Dvořák, A. Holý, Tetrahedron Lett. 1996, 37, 1285-1288;
43. f) H. Dvořáková, D. Dvořák, A. Holý, Collect. Czech. Chem. Commun. 1998, 63, 2065-2074;
44. g) M. Hocek, H. Dvořáková, J. Org. Chem. 2003, 68, 5773-5776.
45. a) A. Suzuki, Acc. Chem. Res. 1982, 15, 178-184;
46. b) A. Suzuki, Pure Appl. Chem. 1994, 66, 213-222;
47. c) A. Suzuki, Pure Appl. Chem. 1985, 57, 1749-1758;
48. d) A. Suzuki, Pure Appl. Chem. 1991, 63, 419-422;
49. e) A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168;
50. f) V. Sniekus, Chem. Rev. 1990, 90, 879-933;
51. g) D. S. Matteson, Tetrahedron 1989, 45, 1859-1885;
52. h) S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. Int. Ed. 2001, 40, 4544-4568;
53. i) N. Miyaura; A. Suzuki, Chem. Commun. 1979, 19, 866-867;
54. j) N. Miyaura, K. Yamada, A. Suzuki, Tetrahedron Lett. 1979, 20, 3437-3440;
55. k) N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513-519;
56. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1470;
57. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
58. a) M. Havelková, D. Dvořák, M. Hocek, Synthesis 2001, 1704-1710;
59. b) M. Havelková, M. Hocek, M. Česnek, D. Dvořák, Synlett 1999, 1145-1147;
60. c) M. Hocek, A. Holý, I. Votruba, H. Dvořá ková, Collect. Czech. Chem. Commun. 2000, 65, 1683-1697;
61. d) M. Hocek, A. Holý, I. Votruba, H. Dvořá ková, Collect. Czech. Chem. Commun. 2001, 66, 483-499.
62. a) L. A. Agrofoglio, I. Gillaizeau, Y. Saito, Chem. Rev. 2003, 103, 1875-1916;
63. b) M. Hocek, Eur. J. Org. Chem. 2003, 245-254;
64. c) M. K. Lakshman, J. Organomet. Chem. 2002, 653, 234-251;
65. d) M. K. Lakshman, J. H. Hilmer, J. Q. Martin, J. C. Keeler, Y. Q. V. Dinh, F. N. Ngassa, L. M. Russon, J. Am. Chem. Soc. 2001, 123, 7779-7787;
66. e) S. Ding, N. S. Gray, Q. Ding, P. G. Schultz, Tetrahedron Lett. 2001, 42, 8751-8755;
67. f) E. C. Western, J. R. Daft, E. M. Johnson, II, P. M. Gannett, K. H. Shaughnessy, J. Org. Chem. 2003, 68, 6767-6774.
68. N. Whittaker, T. S. G. Jones, J. Chem. Soc. 1951, 1565-1570.
69. a) K. Ohno, W. Ishida, K. Kamata, K. Oda, M. Machida, Heterocycles 2003, 59, 317-322;
70. b) N. B. Ambati, V. N. S. R. Babu, V. Anand, P. Hanumanthu, Synthetic Commun. 1999, 29, 289-294;
71. c) D. H. Swenson, K. El-Bayoumy, G.-H. Shuie, S. S. Hecht, E. Fiala, F. F. Kadlubar, J. P. Freeman, Chem. Res. Toxicol. 1993, 6, 480-485;
72. d) J. Valdez, R. Cedillo, A. Hernández-Campos, L. Yépez, F. Hernández-Luis, G. Navarrete-Vázquez, A. Tapia, R. Cortés, M. Hernández, R. Castillo, Bioorg. & Med. Chem. Lett. 2002, 12, 2221-2224;
73. e) B. Singh, G. Y. Lesher, Synthesis 1991, 3, 211-213.
74. a) D. Badone, M. Baroni, R. Cardamone, A. Ielmini, U. Guzzi, J. Org. Chem. 1997, 62, 7170-7173;
75. b) N. E. Leadbeater, M. Marco, J. Org. Chem. 2003, 68, 5660-5667.
76. The reaction rate strongly depends on the particle size of inorganic base (40-70 μm).
77. D. J. Ager, M. B. East, A. Eisenstadt, S. A. Laneman, Chem. Commun. 1997, 24, 2359-2360.
78. W. Shen, Tetrahedron Lett. 1997, 38, 5575-5578.
79. J. H. L. Ong, C. Nataro, J. A. Golen, A. L. Rheingold, Organometallics 2003, 22, 5027-5032.
80. a) W. R. Cullen, T. J. Kim, F. W. B. Einstein, T. Jones, Organometallics 1983, 2, 714-719;
81. b) I. R. Butler, W. R. Cullen, T. J. Kim, S. J. Rettig, J. Trotter, Organometallics 1985, 4, 972-980;
82. c) B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 7369-7370;
83. d) M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 1473-1478;
84. e) S. V. Gagnier, R. C. Larock, J. Org. Chem. 2000, 65, 1525-1529.
85. N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566.
86. THF (86% yield), dimethoxyethane (86% yield), diethoxyethane (88% yield), toluene (78% yield) were also acceptable solvents.
87. J. Clark, P. N. T. Murdoch, D. L. Roberts, J. Chem. Soc. C: Org. 1969, 1408-1412.
88. C. L. Duc, C. Charlon, P. DeMenge, C. A. DeLord, Farmaco, Edizione Scientifica 1978, 33, 516-521.
89. a) D. H. Swenson, K. El-Bayoumy, G-.H. Shuie, S. S. Hecht, E. Fiala, F. F. Kadlubar, J. P. Freeman, Chem. Res. Toxicol. 1993, 6, 480-485;
90. b) J. Garin, E. Melendez, F. L. Merchan, T. Tejero, Synthesis 1985, 867-870.
91. G. Levin, A. Kalmus, F. Bergmann, J. Org. Chem. 1960, 25, 1752-1754.