Aniline → HCID 178420746, compound

Participants

Reaction Conditions

Reaction Steps

Aniline (1.6 g, 17.5 mMol) and 1.0 g (3.5 mMol) 7-chloro-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine were suspended in 100 mL water and heated at 100° C. oil bath for two days. The oil bath temperature was raised to 130° C. and the reaction was continued for two days, when 2 equivalents of aniline were added. On the tenth day of heating, 5 equivalents of aniline were added and the reaction continued for six hours more. The mixture was concentrated in vacuo to give a dark oil. Chromatography twice on silica gel using CHCl3 /CH3OH (9:1) gave nearly pure 7-anilino-3-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine. This was crystallized in two batches from methanol. Total yield was 0.307 g, 18%; m.p. 186°-187° C. The NMR, UV and HPLC retention time were identical to the product prepared enzymatically.

Provenance & Evidence