Trifluoroacetic acid → 10-(5-Chlorofuran-2-yl)-8-((1,3-dioxoisoindolin-2-yl)methyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-7,8-dihydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]thiazine-2,4(3H,10H)-dione

Participants

Reaction Steps

Trifluoroacetic acid (0.399 ml, 5.18 mmol) was added to a solution of 6-(3-(1,3-dioxoisoindolin-2-yl)-2-(tritylthio)propyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (764 mg, 1.035 mmol) in toluene (15 ml) and the mixture was stirred at room temperature for 30 minutes. Bismuth triflate (340 mg, 0.518 mmol) and 5-chlorofuran-2-carbaldehyde (203 mg, 1.553 mmol) were then added and the mixture was stirred at room temperature for 16 hours. The mixture was then diluted with ethyl acetate (150 ml) and washed with water (150 ml), saturated NaHCO3(aq) (150 ml) and brine (150 ml). The organic layer was dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-100% EtOAc/hexane, afforded the title compound as a mixture of diastereomers.

Provenance & Evidence