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Purine acyclic nucleosides. Unambiguous synthesis of acyclovir via a furazano[3,4‐ d ]pyrimidine
Author(s) -
Kelley James L.,
Schaeffer Howard J.
Publication year - 1986
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.5570230156
Subject(s) - chemistry , pyrimidine , purine , alkylation , guanine , reductive amination , hydrolysis , ring (chemistry) , amination , cleavage (geology) , stereochemistry , ammonia , uracil , alkoxy group , medicinal chemistry , organic chemistry , nucleotide , dna , catalysis , biochemistry , alkyl , geotechnical engineering , fracture (geology) , engineering , gene , enzyme
Acyclovir was synthesized in five steps from 7‐formamido‐5‐methylthiofurazano[3,4‐ d ]pyrimidine 2 . Alkylation of 2 with 2‐(benzoyloxy)ethoxymethyl chloride, followed by reductive cleavage of the furazan ring gave 9‐[[2‐(benzoyloxy)ethoxy]methyl]‐2‐(methylthio)adenine 5 . Hydrolysis of the 6‐amino group of 5 , followed by amination of 7 with ammonia gave 9‐[(2‐hydroxyethoxy)methyl]guanine ( 1 , acyclovir).