2-Bromo-4-chloro-1,3-thiazole → 6-(3-(4-Chlorothiazol-2-yl)-3-oxopropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Participants

Reaction Steps

Isopropylmagnesium chloride lithium chloride complex solution (1.3M, 2.93 mL, 3.81 mmol) was added dropwise to a solution of 3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)-N-methoxy-N-methylpropanamide (470 mg, 1.269 mmol) and 2-bromo-4-chlorothiazole (Intermediate Q) (252 mg, 1.269 mmol) in THF (20 mL). The mixture was stirred at room temperature for 45 mins. The reaction was quenched with saturated NH4Cl(aq) and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 20-70% EtOAc/hexane afforded the title compound.

Provenance & Evidence