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Acyclo analogs of formycin a
Author(s) -
Griengl H.,
Günzl F.
Publication year - 1984
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.5570210247
Subject(s) - chemistry , methanol , methyl iodide , potassium carbonate , ethylene glycol , pyrimidine , ammonia , methylation , medicinal chemistry , potassium , chloride , organic chemistry , stereochemistry , biochemistry , gene
Starting from 7‐chloro‐3‐methyl‐1 H ‐pyrazolo[4,3‐ d ]pyrimidine ( 1 ) by reaction with methanol/hydrogen chloride, subsequent methylation and reaction with N ‐bromosuccinimide 3‐bromomethyl‐7‐methoxy‐1‐methyl‐1 H ‐pyrazolo[4,3‐ d ]pyrimidine ( 6 ) is prepared. Treatment with ethylene glycol in the presence of potassium carbonate/potassium iodide and subsequent reaction with ethanolic ammonia afforded 7‐amino‐3‐(2‐hydroxyethoxymethyl)‐1‐methyl‐1 H ‐pyrazolo[4,3‐ d ]pyrimidine ( 11 ) an acyclo analog of formycin A.