Tetrahydrofuran → 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-((2,2-diphenylethyl)amino)-N-(2-(piperidin-1-yl)ethyl)-9H-purine-2-carboxamide

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Reaction Steps

A solution of (2R,3R,4S,5R)-2-{6-[(2,2-diphenylethyl)amino]-2-iodo-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol (59, 8.7 mmol) (Preparation 2), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) (1:1 complex with dichloromethane) (0.7 g, 0.9 mmol) and 1-(2-aminoethyl)piperidine (3.49, 26.5 mmol) in anhydrous tetrahydrofuran (250 ml) was heated at 60° C., under a carbon monoxide atmosphere at 345 kPa (50 psi) in a sealed vessel for 24 hours. The mixture was cooled, filtered through a pad of Arbocel (trade mark) and the filtrate diluted with tetrahydrofuran (150 ml) and ethyl acetate (400 ml). The resulting solution was washed with water (3×300 ml) and the organic phase extracted with 2 M aqueous hydrochloric acid solution (50 ml). The acidic aqueous phase was washed with ethyl acetate (20 ml) then the pH adjusted to >7 by addition of 0.88 aqueous ammonia solution. Ethyl acetate (100 ml) was added and the mixture stirred for 10 minutes after which time a white solid formed. This solid was filtered, washed sequentially with water and ethyl acetate and dried at 70° C. under reduced pressure to yield the title compound as a white solid (2.8 g).

Provenance & Evidence