Abstract
Functionally 4,6-disubstituted 1H-pyrazolo[3,4-d]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1H-pyrazolo[3,4-d]pyrimidines are practically unexplored derivatives in this series. In this paper, it was shown that the nucleophilic substitution of 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine with methylamine produced selectively 4-substituted product, 6-(chloromethyl)-N,1-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine. The structure of the synthesized compound was established by elemental analysis, high resolution mass-spectrometry, 1H, 13C-NMR, and IR spectroscopy, mass-spectrometry, and X-ray analysis.
Highlights
We recently reported on the synthesis of 4-chloro-6-(chloromethyl)-1-methyl-1Hpyrazolo[3,4-d]pyrimidine which has two centers for nucleophilic substitution of chlorine atoms [6]
4-chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine, was studied in the reaction of nucleophilic substitution with amines which led to disubstituted products with equal substituents in the pyrimidine ring and 2-methylene groups [5]
Pyrimidine 1, which contains two reactive chlorine atoms in the 4 position of pyrimidine ring and in CH2 Cl group with methylamine was examined in this paper
Summary
1H-Pyrazolo[3,4-d]pyrimidines have attracted great interest as purine analogs They exhibited various biological activities, including anti-inflammatory [1], antiproliferative [2], antifungal [3], and many other activities [4]. 4,6-disubstituted 1-phenyl-1Hpyrazolo[3,4-d]pyrimidines showed good antibacterial and anticancer activity [5]. New derivatives of this class can be considered as compounds with great potential for biological activity. We recently reported on the synthesis of 4-chloro-6-(chloromethyl)-1-methyl-1Hpyrazolo[3,4-d]pyrimidine which has two centers for nucleophilic substitution of chlorine atoms [6]. We report the reaction of 4-chloro-6-(chloromethyl)-1methyl-1H-pyrazolo[3,4-d]pyrimidine with methylamine and the regioselective synthesis of 6-(chloromethyl)-N,1-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound can be considered as an important intermediate for the preparation of previously inaccessible disubstituted 1H-pyrazolo[3,4-d]pyrimidines
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