Utility of 4,6-dichloro-2-(methylthio)-5-nitropyrimidine. Part 2: Solution phase synthesis of tetrasubstituted purines |
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Authors: | Lars GJ HammarströmMichael E Meyer David B Smith Francisco X Talamás |
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Institution: | Roche Palo Alto, 3431 Hillview Avenue, Palo Alto, CA 94304, USA |
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Abstract: | A simple synthesis of tetrasubstituted purines is disclosed based on the solution phase elaboration of 4,6-dichloro-2-methylthio-5-nitropyrimidine. One-pot sequential C4 and C6 chloride substitution by secondary and primary amines yields 4,6-diamino-2-methylthio-5-nitropyrimidines. mCPBA-mediated oxidation of the methylthio moiety to the corresponding sulfone allows facile substitution at the 2-position. CrCl2 assisted reduction of the nitro group, followed by acid catalyzed orthoester cyclization, then provides novel tetrasubstituted purines not accessible by other methods. |
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