5-chloro-7-anilino-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine → HCID 14391767, compound

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Reaction Steps

A solution of 5-chloro-7-anilino-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine (0.104 g, 0.28 mMol) in 150 mL of water containing 0.1 g of 10% palladium on carbon was hydrogenated in a Parr apparatus for 120 h at 45 psi. The catalyst was removed by filtration and washed well with water. The aqueous filtrate was taken to dryness in vacuo and the residue recrystallized from a minimum of boiling water to give 13 mg of 7-anilino-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine as shown by retention time on reversed phase HPLC and the following: UV max (nm) at pH 1, 304; at pH 13, 301; NMR (DMSO-d6): 9.06 δ (s, 1H, NH); 8.43 (s, 1H, H2); 7.97 (d, 1H, J=5.66 Hz, H5); 7.40-7.07 (m, 5H, Phenyl); 6.88 (d, 1H, J=5.83 Hz, H6); 5.97 (d, 1H, J=6.32 Hz H1').

Provenance & Evidence