6-(Chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine
Functionally 4,6-disubstituted 1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidines are practically unexplored d...
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| Format: | Article |
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MDPI AG
2021-11-01
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| Online Access: | https://www.mdpi.com/1422-8599/2021/4/M1294 |
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| author | Vladimir A. Ogurtsov Oleg A. Rakitin |
| author_facet | Vladimir A. Ogurtsov Oleg A. Rakitin |
| author_sort | Vladimir A. Ogurtsov |
| collection | DOAJ |
| description | Functionally 4,6-disubstituted 1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1<i>H</i>-pyrazolo[3,4-<i>d</i>]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-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidine with methylamine produced selectively 4-substituted product, 6-(chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine. The structure of the synthesized compound was established by elemental analysis, high resolution mass-spectrometry, <sup>1</sup>H, <sup>13</sup>C-NMR, and IR spectroscopy, mass-spectrometry, and X-ray analysis. |
| first_indexed | 2024-03-10T03:30:48Z |
| format | Article |
| id | doaj.art-e0e9c42bed434ebc805ec2e9ab0a51d2 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-10T03:30:48Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-e0e9c42bed434ebc805ec2e9ab0a51d22023-11-23T09:43:30ZengMDPI AGMolbank1422-85992021-11-0120214M129410.3390/M12946-(Chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amineVladimir A. Ogurtsov0Oleg A. Rakitin1N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, RussiaFunctionally 4,6-disubstituted 1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1<i>H</i>-pyrazolo[3,4-<i>d</i>]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-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidine with methylamine produced selectively 4-substituted product, 6-(chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine. The structure of the synthesized compound was established by elemental analysis, high resolution mass-spectrometry, <sup>1</sup>H, <sup>13</sup>C-NMR, and IR spectroscopy, mass-spectrometry, and X-ray analysis.https://www.mdpi.com/1422-8599/2021/4/M12941<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidines6-(chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-aminenucleophilic substitutionX-ray analysisbiological activity |
| spellingShingle | Vladimir A. Ogurtsov Oleg A. Rakitin 6-(Chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine Molbank 1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidines 6-(chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine nucleophilic substitution X-ray analysis biological activity |
| title | 6-(Chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine |
| title_full | 6-(Chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine |
| title_fullStr | 6-(Chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine |
| title_full_unstemmed | 6-(Chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine |
| title_short | 6-(Chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine |
| title_sort | 6 chloromethyl i n i 1 dimethyl 1 i h i pyrazolo 3 4 i d i pyrimidin 4 amine |
| topic | 1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidines 6-(chloromethyl)-<i>N</i>,1-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amine nucleophilic substitution X-ray analysis biological activity |
| url | https://www.mdpi.com/1422-8599/2021/4/M1294 |
| work_keys_str_mv | AT vladimiraogurtsov 6chloromethylini1dimethyl1ihipyrazolo34idipyrimidin4amine AT olegarakitin 6chloromethylini1dimethyl1ihipyrazolo34idipyrimidin4amine |