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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 18
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Original Articles

Synthesis of 8-Bromo-N-benzylpurines via 8-Lithiated Purines: Scope and Limitations

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Pages 2723-2735 | Received 03 Aug 2009, Published online: 09 Aug 2010

REFERENCES

  • For recent reviews, see, for instance , (a) Seela , F. ; Ramzaeva , N. ; Rosemeyer , H. Product class 17: Purines . In Science of Synthesis ; Y. Yamamoto (Ed.); Thieme : Stuttgart , 2004 ; vol. 16 , pp. 945 – 1108 ; (b) Gundersen, L.-L. Metal-mediated C‒C and C‒N bond formation in the synthesis of bioactive purines. Targets Heterocycl. Sys. 2008, 12, 85–119 .
  • Nolsøe , J. M. J. ; Gundersen , L.-L. ; Rise , F. Synthesis of 8-halopurines by reaction of lithiated purines with appropriate halogen donors . Synth. Commun. 1998 , 28 , 4303 – 4315 .
  • Nolsøe , J. M. J. ; Gundersen , L.-L. ; Rise , F. Regiochemistry in Pd-mediated coupling between 6,8-dihalopurines and organometallic reagents . Acta Chem. Scand. 1999 , 53 , 366 – 372 .
  • Brændvang , M. ; Gundersen , L.-L. Synthesis, biological activity, and SAR of antimycobacterial 2- and 8-substituted 6-(2-furyl)-9-(p-methoxybenzyl)purines . Bioorg. Med. Chem. 2007 , 15 , 7144 – 7165 .
  • (a) Kiselgof , E. ; Tulshian , D. B. ; Arik , L. ; Zhang , H. ; Fawzi , A. 6-(2-Furanyl)-9H-purin-2-amine derivatives as A2A adenosine antagonists . Bioorg. Med. Chem. 2005 , 15 , 2119 – 2122 ; (b) Gillespie , R. J. ; Cliffe , I. A. ; Dawson , C. E. ; Dourish , C. T. ; Gaur , S. ; Jordan , A. M. ; Knight , A. R. ; Lerpiniere , J. ; Misra , A. ; Pratt , R. M. ; Roffey , J. ; Stratton , G. C. ; Upton , R. ; Weiss , S. M. ; Williamson , D. S. Antagonists of the human adenosine A2A receptor, part 3: Design and synthesis of pyrazolo[3,4-d]pyrimidines, pyrrolo[2,3-d]pyrimidines, and 6-arylpurines . Bioorg. Med. Chem. 2008 , 18 , 2924 – 2929 .
  • (a) Bakkestuen , A. K. ; Gundersen , L.-L. ; Langli , G. ; Liu , F. ; Nolsøe , J. M. J. 9-Benzylpurines with inhibitory activity against Mycobacterium tuberculosis . Bioorg. Med. Chem. Lett. 2000 , 10 , 1207 – 1210 ; (b) Gundersen , L.-L. ; Nissen-Meyer , J. ; Spilsberg , B. Synthesis and antimycobacterial activity of 6-arylpurines: The requirements for the N-9 substituent in active antimycobacterial purines . J. Med. Chem. 2002 , 45 , 1383 – 1386 ; (c) Bakkestuen , A. K. ; Gundersen , L.-L. ; Utenova , B. T. Synthesis, biological activity, and SAR of antimycobacterial 9-aryl-, 9-arylsulfonyl-, and 9-benzyl-6-(2-furyl)purines . J. Med. Chem. 2005 , 48 , 2710 – 2723 ; (d) Brændvang , M. ; Gundersen , L.-L. Selective anti-tubercular purines: Synthesis and chemotherapeutic properties of 6-aryl- and 6-heteroaryl-9-benzylpurines . Bioorg. Med. Chem. 2005 , 13 , 6360 – 6373 .
  • Bråthe , A. ; Gundersen , L.-L. ; Malterud , K. E. ; Rise , F. 6-Substituted purines as inhibitors of 15-lipoxygenase: A structure–activity study. Arch. Pharm. Chem. Life Sci. 2005, 338, 159–166.
  • (a) Nair , V. ; Uchil , V. ; Neamati , N. β-Diketo acids with purine nucleobase scaffolds: Novel, selective inhibitors of the strand transfer step of HIV integrase . Bioorg. Med. Chem. Lett. 2006 , 16 , 1920 – 1923 ; (b) Alonso , N. ; Caamano , O. ; Fernandez , F. ; Garcia-Mera , X. ; Morales , M. ; Rodriguea-Borges , J. E. ; De Clercq , E. Synthesis and antiviral activities of novel purinyl- and pyrimidinylcarbanucleosides derived from indan . Synthesis 2008 , 1845 – 1852 .
  • (a) Bråthe , A. ; Gundersen , L.-L. ; Nissen-Meyer , J. ; Rise , F. ; Spilsberg , B. Cytotoxic activity of 6-alkynyl- and 6-alkenylpurines . Bioorg. Med. Chem. Lett. 2003 , 13 , 877 – 880 ; (b) Hocek , M. ; Stepnicka , P. ; Ludvik , J. ; Cisaova , I. ; Votruba , I. ; Reha , D. ; Hobza , P. Ferrocene-modified purines as potential electrochemical markers: Synthesis, crystal structures, electrochemistry, and cytostatic activity of (ferrocenylethynyl)- and (ferrocenylethyl)purines . Chemistry 2004 , 10 , 2058 – 2066 ; (c) Kasibhatla , R. S. ; Hong , K. ; Biamonte , M. A. ; Busch , D. J. ; Karjian , P. L. ; Sensintaffar , J. L. ; Kamal , A. ; Lough , R. E. ; Brekken , J. ; Lundgren , K. ; Grecko , R. ; Timony , G. A. ; Ran , Y. ; Mansfield , R. ; Fritz , L. C. ; Ulm , E. ; Burrows , F. J. ; Boehm , M. F. Rationally designed high-affinity 2-amino-6-halopurine heat shock protein 90 inhibitors that exhibit potent antitumor activity . J. Med. Chem. 2007 , 50 , 2767 – 2778 .
  • Duker , N. J. ; Sperling , J. ; Soprano , K. J. ; Druin , D. P. ; Davis , A. ; Ashworth , R. β-Amyloid protein induces the formation of purine dimers in cellular DNA . J. Cell. Biochem. 2001 , 81 , 393 – 400 , and references cited therein .
  • Tobrman , T. ; Stepnicka , P. ; Cisarova , I. ; Dvorak , D. Preparation and crystal structure of purine 2,2′-, 6.6′- and 8,8′-dimers . Eur. J. Org. Chem. 2008 , 2167 – 2174 .
  • Cerna , I. ; Pohl , R. ; Klepetarova , B. ; Hocek , M. Direct C‒H arylation of purines: Development of methodology and its use in regioselective synthesis of 2,6,8-trisubstituted purines . Org. Lett. 2006 , 8 , 5389 – 5392 .
  • McKenzie , T. C. ; Glass , D. The reaction of 6-halopurines with phenyl metal complexes . J. Heterocycl. Chem. 1987 , 24 , 1551 – 1553 .
  • (a) Dvorakova , H. ; Dvorak , D. ; Holy , A. Coupling of 6-chloropurines with organocuprates derived from Grignard reagents: A convenient route to sec and tert 6-alkylpurines . Tetrahedron Lett. 1996 , 37 , 1285 – 1288 ; (b) Klecka , M. ; Tobrman , T. ; Dvorak , D. Cu(I)-catalyzed coupling of (9-benzylpurin-6-yl)magnesium chloride with allyl halides: An approach to 6-allylpurine derivatives . Collect. Czech. Chem. Commun. 2006 , 71 , 1221 – 1228 .
  • See, for instance, (a) Sutcliffe , E. Y. ; Robins , R. K. Electron density and orientation of nucleophilic substitution in the purine ring . J. Org. Chem. 1963 , 28 , 1662 – 1666 ; (b) Barlin , G. B. ; Chapman , N. B. Nucleophilic displacement reactions in aromatic systems, part IX: Kinetics of the reactions of 2-, 6-, or 8-chloro-9-methylpurine with piperidine in ethanol . J. Chem. Soc. 1965 , 3017 – 3022 ; (c) Barlin , G. B. Kinetics of reactions in heterocycles, part IV: The reaction of chloropurines and their 9-methyl derivatives with sodium ethoxide or piperidine . J. Chem. Soc. B 1967 , 954 – 958 ; (d) Gerster , J. F. ; Hinshaw , B. C. ; Robins , R. K. ; Townsend , L. B. Purine nucleosides, XIX: Synthesis of certain 8-chloropurine nucleosides and related derivatives . J. Org. Chem. 1968 , 33 , 1070 – 1073 .
  • (a) Wanner , M. J. ; Von Frijtag Drabbe Künzel , J. K. ; Ijzerman , A. P. ; Koomen , G.-J. 2-Nitro analogues of adenosine and binding studies at the adenosine A1, A2A, and A3 receptor subtypes . Bioorg. Med. Chem. Lett. 2000 , 10 , 2141 – 2144 ; (b) Brændvang , M. ; Gundersen , L.-L. A novel method for the introduction of fluorine in the purine 2-position: Synthesis of 2-fluoroadenosine and a formal synthesis of the antileukemic drug fludarabine . Synthesis 2006 , 2993 – 2995 .
  • Maras , N. ; Polanc , S. ; Kocevar , M. Microwave-assisted methylation of phenols with tetramethylammonium chloride in the presence of K2CO3 or Cs2CO3 . Tetrahedron 2008, 64, 11618–11624.
  • Suzuki , H. ; Tsukuda , A. ; Mika Kondo , M. ; Aizawa , M. ; Senoo , Y. ; Nakajima , M. ; Watanabe , T. ; Yokoyama , Y. ; Murakami , Y. Unexpected debenzylation of N-benzylindoles with lithium base: A new method of N-debenzylation . Tetrahedron Lett. 1995 , 36 , 1671 – 1672 .
  • Li , X. ; Vince , R. Synthesis and biological evaluation of purine derivatives incorporating metal chelating ligands as HIV integrase inhibitors . Bioorg. Med. Chem. 2006 , 14 , 5742 – 5755 .
  • Guthmann , H. ; Könemann , M. ; Bach , T. Synthesis of a cyclic tetrameric purine by successive cross-coupling reactions and subsequent Pd-catalyzed cyclization . Eur. J. Org. Chem. 2007 , 632 – 638 .
  • Gundersen , L.-L. ; Bakkestuen , A. K. ; Aasen , A. J. ; Øverås , H. ; Rise , F. 6-Halopurines in palladium-catalyzed coupling with organotin and organozinc reagents . Tetrahedron 1994 , 50 , 9743 – 9756 .

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