N,N-Dimethylaniline → 4-Chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine

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Reaction Steps

Into a 250 mL round bottom flask was combined 5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidin-4(3H)-one (0.250 g, 1.03 mmol), phosphoryl chloride (0.8 mL, 8 mmol), and 1,2-dichloroethane (10 mL). N,N-Dimethylaniline (0.01 g, 0.1 mmol) was added dropwise and the mixture was heated at reflux for 2 hours. The mixture was reduced in vacuo to yield a dark brown oil. The oil was taken up in methylene chloride (50 mL) and poured over ice. The mixture was carefully neutralized using sat. aq. sodium bicarbonate. The organic layer was separated and dried over sodium sulfate and reduced in vacuo. The residue was purified by flash chromatography on silica gel (0-10% methanol/methylene chloride) to give a bright yellow solid. (0.141 g, 52.4%).

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