[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.[Na].Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=1>C(OCC)(=O)C.O>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=2)[CH2:3][CH2:2]12-Morpholinoethanol (2.2 g, 16.8 mmol) was treated with sodium (116 mg, 5.0 mmol) in a sealed tube and stirred at ambient temperature until homogeneous. 4-Chloropyridin-2-amine (1.1 g, 8.9 mmol) was added and the reaction mixture was heated to 145° C. and stirred in sealed tube for 10 hours. The mixture was cooled to ambient temperature before diluting with ethyl acetate and water. After separation of layers, the aqueous phase was extracted twice more with ethyl acetate. Concentration under vacuum afforded a viscous oil which required purification using a Biotage 40+Silica column eluting with 10% methanol/dichloromethane to give 4-(2-morpholinoethoxy)pyridin-2-amine as a viscous oil which solidified upon further drying under high vacuum (1.4 g).
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