Benzoyl chloride, 3,4,5-trimethoxy- → (2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3,4,5-trimethoxy-phenyl)-methanone

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Reaction Steps

To a mixture of 2-methoxy-7H-pyrrolo[2,3-d]pyrimidine (0.220 g, 1.476 mmol) and anhydrous zinc chloride (0.407 g, 2.953 mmol) in dry CH2Cl2 (20 mL), ethylmagnesium bromide (0.65 mL, 3.0 M solution in diethyl ether) was added over 10 min at room temperature. The suspension was stirred for 1 h, and then 3,4,5-trimethoxybenzoyl chloride (0.510 g, 2.2 mmol) in dry CH2Cl2 (10 mL) was added dropwise over 5 min. The reaction mixture was stirred for another 1 h and then aluminum chloride (0.196 mg, 1.476 mmol) was added. The resulting thick mixture was vigorously stirred for 5 h. The reaction was quenched with water (10 mL) and extracted with CH2Cl2 (20 mL). The combined organic layers were dried over anhydrous MgSO4 and evaporated to give a brown oil, which was purified on a silica gel column (EtOAc:Hexane=1:1 to MeOH:CH2Cl2=1:20) to give compound 16 (0.081 g, 20%).

Provenance & Evidence