Acetoxyacetyl chloride → (7-Mercapto[1,3]thiazolo[5,4-d]pyrimidin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A cooled (ice bath) suspension of 5-aminopyrimidine-4,6-dithiol (Intermediate 41) (40.0 g) in pyridine (500 mL) was stirred under an inert atmosphere atmosphere. Acetoxyacetyl chloride (38 mL) was added over 10 minutes, the ice bath was removed and the mixture stirred at ambient temperature overnight. The mixture was concentrated in vacuo and azeotroped three times with toluene (200 mL). The residue was suspended in 2N HCl, and heated at 115° C. for 5 hours, and allowed to cool to ambient temperature overnight. The resulting suspension was filtered, washed with water (200 mL) and ether (200 mL) to give the title compound as a pale brown solid (48.3 g, 97%) (containing 10% of (7-mercapto[1,3]thiazolo[5,4-d]pyrimidin-2-yl)methyl acetate);

Provenance & Evidence