Acetic Anhydride → 6-chloro-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}pyrido[3,4-d]pyrimidin-4(3H)-one

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Reaction Conditions

Reaction Steps

Using 5-amino-4-carboxy-2-chloropyridine and acetic anhydride as starting materials, 6-chloro-2-methyl-3-(4-hydroxyphenyl)pyrido[3,4-d]pyrimidin-4(3H)-one synthesized according to Example 1-(1) and -(2) (52 mg, 0.18 mmol), 1-(3-bromopropyl)piperidine hydrobromide (78 mg, 0.27 mmol) and potassium carbonate (100 mg, 0.72 mmol) were mixed in dimethylformamide (1 mL) and stirred at 80° C. for 1 hour. The solvent was distilled off under reduced pressure, distilled water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with distilled water, and dried with anhydrous sodium sulfate. The title compound (45 mg, 60%) was obtained as colorless crystals by purifying with silica gel column chromatography (chloroform/methanol=30/1) and recrystallizing (ethanol).

Provenance & Evidence