Water → 3-(1,3-Dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A suspension comprising 1,3-dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid (Intermediate F) (300 mg, 0.571 mmol), 3-bromobenzonitrile (104 mg, 0.571 mmol) and barium hydroxide (196 mg, 1.142 mmol) in n-BuOAc (5710 μL) was treated with Pd-118 (18.61 mg, 0.029 mmol) and the mixture was heated to 80° C. Water (247 μL, 13.70 mmol) was added at 80° C. and the suspension was stirred rapidly for 90 minutes. After cooling to RT, the mixture was allowed to stand at RT overnight. The mixture was diluted with DCM (50 ml) and washed with water (50 ml). The layers were separated and the aqueous portion was extracted with DCM (3×30 ml). The organics were combined and dried over MgSO4, filtered and concentrated. Purification of the crude product by trituration with EtOAc/iso-hexane afforded the title compound;

Provenance & Evidence