Synthesis of pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-ones |
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Authors: | Sergey V. Ryabukhin Dmitry S. Granat Andrey S. Plaskon Alexander Shivanyuk Oleg Lukin |
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Affiliation: | 1. The Institute of High Technologies, Kiev National Taras Shevchenko University, Glushkov St., Building 5, Kiev 01033, Ukraine;2. Department of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska St. 64, Kiev 01033, Ukraine;3. Curplyx Drs, JSC Macrochem, Lunacharsky St. 4, 7th Floor, Kiev 02002, Ukraine |
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Abstract: | A small library of hitherto unprepared pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-ones was synthesized on a preparative scale. The synthesis starts with a substituted 5-aminopyrazole that reacts with an isocyanate to give the corresponding urea. The latter undergoes a chlorotrimethylsilane-promoted [5+1] cyclocondensation with an aldehyde yielding the title pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-one. Both synthetic steps are high-yielding (74–94%). The intermediates and the target compounds were isolated by simple crystallization. Ketones with the exception of isatin do not react with the open-chain urea intermediates. |
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Keywords: | Aldehydes Aminopyrazoles Dihydropyrimidines Ureas Chlorotrimethylsilane |
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