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Synthesis 1995; 1995(7): 837-840
DOI: 10.1055/s-1995-3996
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New [c,d]-Fused Purinediones: 2-Substituted 9-Methyl-4,5-dihydro-6H,8H-pyrimido-[1,2,3-cd]purine-8,10(9H)-diones

Ondrej Šimo, Alfonz Rybár* , Juraj Alföldi
  • *Institute of Chemistry, Slovak Academy of Sciences, SK-84238 Bratislava, The Slovak Republic, Fax +42(7)373811; E-mail chembabo@savba.savba.sk
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Publikationsdatum:
31. Dezember 2000 (online)

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2-Alkyl- or 2-aryl-9-methyl-4,5-dihydro-6H,8H-pyrimido[1,2,3-cd]purine-8,10(9H)-diones 5 were obtained either by a four-step synthesis starting from 6-chloro-5-nitro-3-methylpyrimidine-2,4(1H,3H)-dione (1) via 9-amino-7-methyl-3,4-dihydro-2H-pyrimido[1,6-a]pyrimidine-6,8(1H,7H)-dione (4) and its reaction with the respective orthocarboxylates, or, alternatively, by a four-step process from 6-[(3-hydroxypropyl)amino]-3-methyl-5-nitrosopyrimidine-2,4(1H,3H)-dione via 8-alkyl- or 8-aryl-9-mesyloxypropyl-1-methyl-3,9-dihydro-1H-purine-2,6-diones 9 and their intramolecular alkylation in dimethylformamide (DMF) in the presence of potassium carbonate.

pyrimido-[1,2,3-cd]purinediones - pyrimido-[1,6-a]purinediones - 9-(3-hydroxypropyl)purinediones - substituted pyrimidinediones - annulation of N-heterocycles