Methanol → 2-Thioadenosine

Participants

Reaction Steps

8.0 g of adenosine 1-oxide (26.67 mmol) was refluxed in 75 ml of a 5N sodium hydroxide aqueous solution for 15 minutes. The resulting liquid was neutralized to a pH of 5.0 with Amberlite IRC-50 (H+-type) and concentrated to a small volume to prepare 1-β-D-ribofuranosyl-5-aminoimidazole-4-carboxamide oxime. To this was added 200 ml of an aqueous solution containing 175 ml of methanol, the resulting solution being found to have a pH of 9. 50 ml of carbon disulfide was added to the solution, and the mixture was allowed to react in an autoclave at 120° C for 5 hours under autogenous pressure (about 10 Kg/cm2). The orange colored substance formed was removed and concentrated to dryness. The residue was dissolved in 63 ml of 2.5N aqueous ammonia, and any impurities were filtered out. A mixture of n-butanol and acetic acid (125 ml: 63 ml) was added to the filtrate to crystallize the product to obtain 5.42 g of 2-thioadenosine having a melting point of 199° C (with decomposition) in a 92% yield.

Provenance & Evidence