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On the syntheses of 8‐Heteroaryl‐substituted 9‐(β‐D‐Ribofuranosyl)‐2,6‐diaminopurines through Pd‐catalyzed coupling in the presence of cupric oxide
Author(s) -
Ozola Vita,
Persson Tina,
Gronowitz Salo,
Hörnfeldt AnnaBritta
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320331
Subject(s) - chemistry , dimethylformamide , catalysis , stille reaction , palladium , reagent , solvent , medicinal chemistry , triethylamine , organic chemistry
Convenient methods for the preparation of 9‐(β‐D‐ribofuranosyl) derivatives of 8‐(2‐ and 3‐thienyl)‐2,6‐diaminopurine and of 8‐(2‐ and 3‐furyl)‐2,6‐diaminopurine, which are potential antiviral agents has been worked out. The key step was a Pd(0)‐catalyzed Stille coupling between 2‐ and 3‐tributylstannylthiophene and 2‐ and 3‐tributylstannylfuran and trimethylsilyl protected 9‐(β‐D‐ribofuranosyl)‐2,6‐diamino‐8‐bro‐mopurine. The use of N , N ‐dimethylformamide as solvent at 110° and dichloro(diphenylphosphine‐propane)palladium(II) [PdC1 2 (dppp)] with cupric oxide as co‐reagent was essential in order to obtain a fast reaction and high yields.