Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- → Methyl 3-(4-chlorothiazol-2-yl)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)-2,2-dimethylpropanoate

Participants

Reaction Steps

Boron trifluoride THF complex (0.028 mL, 0.255 mmol) was added to a solution of 7-((4-chlorothiazol-2-yl) (hydroxy)methyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (114 mg, 0.283 mmol) and commercially available ((1-methoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane (0.143 mL, 0.707 mmol) in THF (5 mL). The mixture was stirred at room temperature for 5 minutes. The reaction was quenched with saturated NaHCO3(aq) and extracted with DCM (2×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 20-80% EtOAc/hexane afforded the title compound.

Provenance & Evidence