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The Course of N‐Alkylation of 6‐Methylmercaptopurines
Author(s) -
Neiman Z.,
Bergmann F.
Publication year - 1965
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.196500044
Subject(s) - chemistry , alkylation , methyl iodide , methylation , solvent , alkali metal , organic chemistry , halide , medicinal chemistry , catalysis , dna , biochemistry
Reaction of a 6‐methylmercaptopurine with methyl iodide in an aprotic solvent gives only a single methylation product. Both the 7‐ and the 9‐methyl derivatives are alkylated at N‐3. 3‐Methyl‐6‐methylmetcaptopurine is attacked at N‐7, while the 1‐methyl isomer is substituted at position 9. The course of the latter reaction depends markedly on the reaction conditions, as in the presence of an alkali carbonate alkylation takes place at N‐7. The mechanism of these methylations is discussed.