ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Mannich Reaction at 2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the Chromophore of the Ribonucleoside “Q”2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one (6a) reacts with dimethylamine and cyclopentylamine in the presence of formaldehyde to form the Mannich bases 6c and d. From 6c the amine moiety was split off on hydrogenation under pressure. The degradation product was identical with 2-amino-6-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one (6b), which was obtained by unambiguous synthesis. This shows that in contrast to 3,7-dihydropyrrolo[2,3-d]-pyrimidin-4-one, Mannich reaction involving 6a leads to substitution at C-6.
Notes:
2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-on (6a) reagiert mit Dimethylamin und Cyclo-pentylamin in Gegenwart von Formaldehyd zu den Mannich-Basen 6c und d. Aus 6c ließ sich durch Druckhydrierung das Amin abspalten. Das Abbauprodukt war identisch mit 2-Amino-6-methyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-on (6b), das auf eindeutigem Syntheseweg erhalten worden war. Damit wird gezeigt, daß die Mannich-Reaktion bei 6a im Gegensatz zu 3,7-Dihydropyrrolo[2,3-d]pyrimidin-4-on zur Substitution an C-6 führt.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19771100428
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