Ethyl 2-bromo-1,3-thiazole-4-carboxylate → Ethyl 2-(1,3-dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thiazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

(1,3-dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)boronic acid (Intermediate F) (1001 mg, 1.906 mmol), ethyl 2-bromothiazole-4-carboxylate (409 mg, 1.732 mmol), sodium hydrogen carbonate (291 mg, 3.46 mmol) and Pd-118 (113 mg, 0.173 mmol) were suspended in n-butyl acetate (12.3 ml) and heated to 80° C. Water (3.08 ml) was then added and the mixture heated at 80° C. for 21 hours. The mixture was then cooled to room temperature and diluted with water (100 ml) and DCM (100 ml). The mixture was extracted with DCM (3×100 ml) and the combined organic extracts were washed with water (50 ml) and brine (50 ml). Silica-TMT (30 g) was added and the mixture stirred at room temperature for 5 mins, then filtered. The residue was rinsed with DCM (20 ml) and the filtrates evaporated under vacuum. The resultant residue was rinsed with diethyl ether and filtered to afford the title compound.

Provenance & Evidence