To a solution of 2-[1-(piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 18) (19.9 mg, 0.062 mmol) in 1,2-dichloroethane (0.5 mL) was added benzaldehyde (6.3 μL, 0.062 mmol) and stirred for 10 min at room temperature. This was followed by the addition of sodium triacetoxyborohydride (18.4 mg, 0.087 mmol) and the reaction mixture was stirred for 3 h. The reaction mixture was quenched with saturated aqueous NaHCO3 and was extracted with EtOAc (3×5 mL). The combined extracts were washed with brine and dried over Na2SO4. The crude product was purified by preparative thin layer chromatography eluting with 1:9 MeOH:CH2Cl2 to obtain 17.9 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.35 (br s, 1H); 8.16 (d, J=7.5 Hz, 1H); 7.86 (d, J=8.9 Hz, 1H); 7.38 (m, 2H); 7.25 (m, 5H); 6.76 (d, J=5.5 Hz, 1H); 4.16 (m, 1H); 3.5 (Abq, JAB=13.2 Hz, 2H); 2.91 (d, J=10.5 Hz, 1H); 2.76 (d, J=11.2 Hz, 1H); 1.23 (d, J=6.6 Hz, 3H). Mass spectrum 413.4 (ESI, M+1).
