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Paper | Special issue | Vol 90, No. 1, 2015, pp.216-225
Published online, 18th March, 2014
DOI: 10.3987/COM-14-S(K)5
Synthesis of 7-Alkyl-6-amino-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitriles by the Copper-Catalyzed Reaction of 4-(Alkylamino)-5-iodopyrimidines with Propanedinitrile

Kazuhiro Kobayashi,* Kazuya Nakazawa, Shohei Yuba, Hidetaka Hiyoshi, and Kazuto Umezu

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A convenient sequence for the first general preparation of 6-aminopyrrolo[2,3-d]pyrimidine-5-carbonitrile derivatives has been developed. Thus, treatment of 4-chloro-6-methoxypyrimidines with lithium diisopropylamide in THF at –78 °C lithiated the 5-position to generate 4-chloro-5-lithio-6-methoxypyrimidines, which were allowed to react with iodine to give 4-chloro-5-iodo-6-methoxypyrimidines in good yields. Substitution of the 4-chloro group of these compounds with primary amines in the presence of triethylamine in refluxing THF afforded 4-(alkylamino)-5-iodo-6-methoxypyrimidines. The reaction of these aminated compounds with propanedinitrile (malononitrile) in the presence of a catalytic amount of copper(I) iodide and excess potassium carbonate in dimethyl sulfoxide at 100 °C provided 7-alkyl-6-amino-4-methoxypyrrolo[2,3-d]pyrimidine-5-carbonitriles in moderate yields.