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Preparation, structural characterization, and acid‐catalyzed isomerization of 3‐, 7‐, and 9‐benzyl‐6‐benzylthiopurines
Author(s) -
Huang Jim J.,
Ragouzeos Aris,
Rideout Janet L.
Publication year - 1994
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.5570310669
Subject(s) - chemistry , isomerization , catalysis , purine , nuclear magnetic resonance spectroscopy , base (topology) , high performance liquid chromatography , stereochemistry , characterization (materials science) , medicinal chemistry , organic chemistry , nanotechnology , mathematical analysis , materials science , mathematics , enzyme
Benzylation of 6‐benzylthiopurine was examined. Structural assignments of the products were determined by 1‐D and 2‐D nmr spectroscopy (HMQC, HMBC, and nOe). In the presence of base, the isomeric N3‐, N7‐, and N9‐benzylated products 4, 3 , and 2 were isolated; however, only 9‐benzyl‐6‐benzylthio‐purine ( 2 ) was obtained in the absence of base. In the latter case, the initially formed N3‐ and N7‐isomers were, in the presence of acid, converted to 9‐benzyl‐6‐benzylthiopurine ( 2 ) via a 6‐benzylthiopurine intermediate as evidenced by analysis of the reaction over time using reversed‐phase hplc.