Chemie polyfunktioneller Moleküle, 74 [1]. Synthese, Umlagerung und Eigenschaften diphenylphosphinosubstituierter Uracile / Chemistry of Polyfunctional Molecules, 74 [1]. Synthesis, Rearrangement and Properties of Diphenylphosphino Substituted Uracils

Abstract

Abstract 5-Bromo-uracil (2) with chloro-diphenylphosphine and triethylamine gives 5-bromo-N(1),N(3)-bis(diphenylphosphino)-uracil (3). In moist acetone, 3 is hydrolyzed to 5-bromo-N(1)-diphenylphosphino-uracil (4). 3 reacts with n-butyllithium under rearrangement and, with HCl, under elimination of a PPh2-group, forms C(5)-diphenylphosphino-uracil (7a). Recrystallization of 7 a from ethanol yields the ethanol-1:1-adduct 7b. Heating of 7a in dimethylsulfoxide with D2O yields the N(1),N(3)-dideutero-C(5)-diphenylphosphino-uracil (7c). All compounds were characterized by infrared, Raman, 1H, 31P NMR and mass spectra. 7a shows a very small antitumor activity.