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Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5‐nitroso
Author(s) -
Melguizo Group M.,
Marchal A.,
Nogueras M.,
Sánchez A.,
Low J. N.
Publication year - 2002
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.5570390114
Subject(s) - chemistry , aminolysis , pyrimidine , moiety , nitroso , ring (chemistry) , nucleophile , glycosyl , medicinal chemistry , organic chemistry , stereochemistry , catalysis
The nucleophilic substitution of 2‐mefhoxy groups in pyrimidine derivatives was strongly activated by introduction of a 5‐nitroso group on to the pyrimidine ring. The aminolysis of several 2‐methoxy‐5‐nitrosopyrimidine derivatives was performed at room temperature in hydroxylic as well as in non‐hydroxylic media with different primary amines in short time and good yields. The aminolysed substrates include 6‐[(per‐ O ‐acetyl)glycosyl]aminopyrimidines which afforded the corresponding 2‐aminopyrimidines without harming the acetyl protecting groups of the sugar moiety.