Cytidine → HCID 54146375, compound

Participants

Reaction Steps

A solution of 17.5 g. (72 millimoles) of cytidine in 540 ml. of water was hydrogenated in a Parr hydrogenator at 30 psi pressure, in the presence of 3.6 g. of 5% rhodium on alumina catalyst. Hydrogen uptake overnight (18-19 hours) was approximately 2 molar equivalents. The solution (pH 10.5) was filtered through a bed of Celite (diatomaceous earth) filter and lyophilized to yield 4-amino-1-β-D-ribofuranosyl-tetrahydro-2(1H)-pyrimidinone as a white amorphous solid. When examined by nuclear magnetic resonance the solid showed a doublet at 5.95 ppm. (anomeric proton); multiplet at 4.50 ppm. ##STR12## multiplets at 3.45 ppm. (--CH2N=) and 2.00 ppm. (C--CH2 --C) and a small amount of absorption at 2.75 ppm. ##STR13## Upon acidification, the 4.50 ppm. multiplet moved downfield to 5.08 ppm. ##STR14## and part of the 2.00 ppm. multiplet moved slightly downfield to 2.2 ppm. Peak locations are referred to the peak for sodium-2,2-dimethyl-2-silapentane-5-sulfonate (SDSS) as internal standard. Held in aqueous solution at pH 5.5 to 6 overnight, the solid was converted to and gave the analytical characteristics of 4-hydroxy-1-β-D-ribofuranosyl-tetrahydro-2(1H)-pyrimidinone.

Provenance & Evidence