Alkylation of some 6-substituted purines under interphase catalysis conditions

Autor: Ramzaeva, N. P., Goncharova, I. N., Lidak, M. Yu., Gol'dberg, Yu. Sh., Shimanskaya, M. V.
Zdroj: Chemistry of Heterocyclic Compounds; January 1987, Vol. 23 Issue: 1 p93-98, 6p
Abstrakt: The mixture of 9-, 3-, and 7-benzyl-6-substituted purines is formed in almost quantitative yield by the alkylation of 6-benzylamino-, 6-furfurylamino-, 6-methylthio-, and 6-chloropurine with benzyl halides in the biphasic system of the liquid-liquid or liquid-solid type in the presence of interphase catalysts (quaternary ammonium salts, 18-crown-6). The catalytic activity of the quaternary ammonium salts increases with the increase in the lipophilicity of the cation. Taking the alkylation of 6-benzylaminopurine as an example, the possibility of the application of “triphasic catalysis” in the alkylation reaction of purines is indicated. The alkylation of 6-substituted purines with isopropyl bromide proceeds regioselectively under the conditions of the interphase catalysis with the formation of the corresponding 9-isopropylpurines.
Databáze: Supplemental Index