Sodium borohydride → HCID 24896977, compound

Participants

Reaction Steps

Sodium periodate (0.070 g, 0.326 mmol) was added to a solution of (2S,3S,4R,5S)-2-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(methylthiomethyl)pyrrolidine-3,4-diol dihydrochloride (0.1 g, 0.272 mmol, prepared according to G. B. Evans, R. H. Furneaux, V. L. Schramm, V. Singh, P. C. Tyler, J. Med. Chem., 2004, 47, 3275) in water (3 ml) and stirred at rt for 1 h. Sodium borohydride (0.051 g, 1.358 mmol) was added in small portions (vigorous reaction). The solution, which momentarily darkened then became almost colourless, was stirred for 15 mins. Silica gel was added and the solvent evaporated. The residue was chromatographed on silica gel (CH2Cl2-MeOH-28% aq. NH4OH, 50:10:1) and the fractions containing product were evaporated to a gum (70 mg) which was dissolved in MeOH and passed through Amberlyst A26 (OH−) resin using MeOH as eluant. The solvent was evaporated to a yellow gum, dissolved in water and lyophilised to give (S)-2-((S)-1-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-2-hydroxyethylamino)-3-(methylthio)propan-1-ol as a cream coloured solid (38 mg, 47%).

Provenance & Evidence