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Pyrazolopyrimidine nucleosides. Part VIII The synthesis of certain 4‐substituted pyrazolo[3,4‐ d ]pyrimidine nucleosides
Author(s) -
Montero Jean Louis G.,
Bhat Ganapati A.,
Panzica Raymond P.,
Townsend Leroy B.
Publication year - 1977
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.5570140326
Subject(s) - chemistry , pyrimidine , nucleoside , aryl , stereochemistry , riboside , alkyl , organic chemistry , biochemistry
1‐(β‐D‐Ribofuranosyl)pyrazolo[3,4‐ b ]pyrimidine‐4‐thione ( 6 ), obtained by a three‐step synthesis from allopurinol riboside (3), was treated with certain alkyl and aryl halides to provide the corresponding 4‐alkylthio derivatives. The nucleoside 4‐methylthio‐1‐(β‐D‐ribofuranosyl)pyra‐zolo[3,4‐ d ]pyritnidine ( 7 ) has served as the precursor for the preparation of the 4‐methylamino ( 11 ), 4‐dimethylamino ( 12 ), 4‐hydrazino ( 13 ), and the 4‐hydroxylamino ( 14 ) analogs.