C-(6-BROMO-PYRIDIN-3-YL)-METHYLAMINE

2-bromo-5-methyl-pyridine (70.0 mmol) and N-bromosuccinimide (80.0 mmol) were dissolved in 1, 2- dichioroethane (150 ml) and to this mixture 2, 2’-azobis(2- ethylpropionitrile) (1.50 mmol) was added. The reaction mixture was heated under reflux at 85° C. for 15 minutes and next portion of 2, 2’-azobis(2-methylpropionitrile) (1.50 mmol) was added and reaction mixture was heated at 85° C. for further 15 minutes. After cooling to room temperature was the reaction mixture kept at 5° C. for 2 hours and the precipitate was filtered off and washed with small amount of 1 , 2-dichlo- roethane. The filtrate was evaporated under reduced pressure and the crude product was used for further reaction step without purification. The crude 2-bromo-5-bromomethyl-py- ridine was dissolved in chloroform (100 ml) and urotropine (70.0 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. The precipitate was filtered off, washed with small amount of chloroform and dried on air. The crude urotropine salt was refluxed in a mixture of conc. ammonium hydroxide (12 ml) and water (80 ml) for 90 minutes and afier cooling to room temperature, 40percent formaldehyde (5.0 ml) was added with stirring. The precipitate was filtered off, washed with ice-cold water and dried in vacuum dessicator. The crude product was crystallized from ethanol. Yield: 40percent m.p. 105-106° C. Elemental analysis: Calcd. for C5H7HrN2 (187.04): C, 38.53; H, 3.77; N, 14.98. Found: C, 38.22; H, 3.72; N, 14.71. HPLC-MS (ESI+): 188.02(97.2percent). ‘H NMR (DMSO, d5): 4.04 (t, J=5.67, 2H, CH2), 7.71 (d, J=8.19, 1H, ArH), 7.95 (dd, J=8.19, J’=i.95, 1H, ArH), 8.51 (d, J=i .95, 1H, ArH), 8.74 (s(br), 2H, NH2).

Molecular Weight:187.04
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:185.97926
Monoisotopic Mass:185.97926
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:87.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes