N,N-Dimethylaniline → 7-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

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Reaction Steps

7-Benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one (9.4 g, 39 mmol) was dissolved in anhydrous 1,2-dichloroethane and stirred under N2(g) atmosphere. To the mixture was added POCl3 (29 mL, 312 mmol), followed by N,N-dimethylaniline (4.75 g, 39 mmol). The mixture was refluxed for 2 h and the solvents were removed under vacuum to give a red residue. The residue was dissolved in 20 mL of ethyl acetate and 20 ml of water was added. The solution was neutralized with ice and solid NaHCO3. After neutralization, ethyl acetate was added and the organic layer was washed with water and brine. The organic layer was dried over Na2SO4 and the solvents were removed under vacuum. The resulting red residue was purified using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as yellow crystals (3.8 g, 38%).

Provenance & Evidence