4-hydrazino-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine → 7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Participants

Reaction Steps

A mixture of 48 g of 4-hydrazino-2-methylmercapto-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine, 500 ml of ethanol, and 100 g of Raney nickel suspension is stirred and heated under reflux for one hour. An additional 100 g of Raney nickel is added and stirring and heating is continued for two hours. The hot suspension is filtered and the filter cake is washed with ethyl acetate. The combined dried filtrates are evaporated in vacuo to 43 g of dark syrup. Chromatography of this material over silica gel with ethyl acetate provides 33 g of pure 7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine. The same compound may also be obtained by hydrogenolysis of 4-hydrazine-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine with Raney nickel.

Provenance & Evidence