Hydrochloric Acid → 6-chloro-N-(2-(methylsulfonyl)ethyl)-2-(4-nitrophenyl)pyrimidin-4-amine

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Reaction Steps

In a 250 mL round-bottom flask was placed 4,6-dichloro-2-(4-nitrophenyl)pyrimidine (59, 500 mg, 1.85 mmol) in dichloromethane (20 mL) to give a colorless solution. 2-(methylsulfonyl)ethanamine.HCl (325 mg, 2.04 mmol) was added followed by addition of triethylamine (0.77 mL, 5.55 mmol). The mixture was stirred at room temperature for 19 hours and was then refluxed for 21 hour. Excess potassium carbonate was added and heating under reflux was continued for 6 hours. The mixture was cooled to room temperature and stirred at room temperature for 2 weeks. The mixture was diluted with dichloromethane and washed with saturated NaHCO3. The organic phase was dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (20-100% ethyl acetate in hexanes) to give the title compound as a yellow solid (196 mg, 30%). HRMS: 357.0417 [M+H]+. For [M+H]+ mass error=−0.2 mDa or −0.60 ppm.

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