[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl:9][C:10]1[CH:15]=[C:14](Cl)[CH:13]=[C:12]([Cl:17])[N:11]=1>CS(C)=O>[Cl:9][C:10]1[CH:15]=[C:14]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:13]=[C:12]([Cl:17])[N:11]=1A mixture of morpholine (0.604 g, 6.04 mmol) in dry DMSO and NaH (0.251 g, 6.6 mmol) was stirred for 30 minutes at 0° C., after which time 2,4,6-trichloropyridine (1.0 g, 5.50 mmol) was added. This reaction mixture was stirred at room temperature for 4 hours, after which time ice cold water was added to quench the reaction (100 mL). The reaction mixture was then extracted with ethyl acetate, and the extract was washed with 3-4 times water. The organic layer was dried over sodium sulphate and concentrated under vacuum. The residue was purified by column chromatography over 100-200 mesh silica gel. Elution of the column with 20% acetone in hexanes gave the pure product as a colorless solid (0.565 g, yield 44%).
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