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A New Synthesis of 4‐(Alkyl)aminopteridines
Author(s) -
Hara Hiroshi,
Van Plas Henk C. Der
Publication year - 1982
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.5570190654
Subject(s) - chemistry , amination , yield (engineering) , alkyl , pteridine , adduct , potassium permanganate , liquid ammonia , medicinal chemistry , organic chemistry , reductive amination , ammonia , potassium , electrophilic amination , catalysis , materials science , metallurgy , enzyme
On treatment of pteridine with potassium permanganate in liquid ammonia, 4‐aminopteridine is obtained in good yield. The C 4 σ adduct 4‐amino‐3,4‐dihydropteridine is the intermediate species. Similarly, 2‐chloropteridine undergoes amination at C 4 , yielding 4‐amino‐2‐chloropteridine; thus no replacement of the chloro atom occurs. By this amination‐oxidation procedure 4‐ethylaminopteridine and its 2‐chloro derivatives are also easily obtained.