Methanol → 2-Thioadenosine

Participants

Reaction Steps

0.45 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide O-ethyl-oxime was dissolved in 8 ml of an aqueous solution containing 7 ml of methanol, and 2 ml of carbon disulfide was added to the solution. The resulting mixture was allowed to react in an autoclave at 120° C for 6 hours under autogenous pressure (about 10 Kg/cm2). The reaction mixture was concentrated to dryness, and the residue was dissolved in water. The aqueous solution was adjusted to a pH of 2 with hydrochloric acid, and the crystals thus precipitated were filtered to obtain 2-thioadenosine, which was then dissolved in aqueous ammonia, filtered and again adjusted to a pH of 2 with hydrochloric acid to obtain 0.355 g of pure 2-thioadenosine having a melting point of 199° C (with decomposition) in a 75% yield.

Provenance & Evidence