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Synthesis of 1‐ and 3‐amino‐5‐t‐butyl‐1H‐ and ‐3H‐v‐triazolo[4,5‐d]pyrimidines as hetaryne precursors
Author(s) -
Tielemans Michel,
Christophe Daniel,
Promel Robert
Publication year - 1987
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.5570240332
Subject(s) - chemistry , hydroxylamine , pyrimidine , hydrochloric acid , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , financial economics , economics
The synthesis of the title compounds 6 and 8 has first been accomplished by reaction of O ‐mesitylsulfonyl‐hydroxylamine with 5‐ t ‐butyl‐3 H ‐ v ‐triazolo[4,5‐ d ]pyrimidine ( 5 ) whose preparation is reported in detail. However the preferred route for the synthesis of the 3‐amino derivative 8 is based upon the preparation of 3‐benzylideneamino‐5‐ t ‐butyl‐3 H ‐ v ‐triazolo[4,5‐ d ]pyrimidine ( 10 ), followed by the removal of the benzylidene protecting group. This critical step was effected by treatment of 10 with dilute hydrochloric acid, in the presence of 2,4‐dinitrophenylhydrazine. The diazotization of 5‐amino‐4‐hydrazino‐2‐ t ‐butylpyrimidine gave predominantly the tetrazolo[1,5‐ c ]‐pyrimidine 13 along with a small amount of compound 8.