2-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine → 2-[1-(1-Benzyloxycarbonylpiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

Participants

Reaction Steps

2-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 1) (1.1 g, 4.0 mmol) was dissolved in DMF (10 mL), and to this was added 3-(1-aminoethyl)-1-(Benzyloxycarbonyl)piperidine (950 mg, 3.6 mmol) in toluene (10 mL). The mixture was placed in an oil bath at 100° C. and heated for 5 h. After cooling, the reaction mixture was diluted with EtOAc (80 mL) and was washed with H2O (4×40 mL) followed by brine. The organic extract was dried over Na2SO4 and purified by flash chromatography using 3:7 acetone:hexane as an eluent to obtain the title compound (900 mg). Partial 1H NMR (500 MHz, CDCl3): δ 8.6 (s, 1H); 8.36 (br s, 1H); 8.15 (d, J=8 Hz, 1H); 7.85 (d, J=8.5 Hz, 1H); 7.36 (m, 7H); 6.76 (d, J=5.4 Hz, 1H); 5.12 (s, 2H); 4.17 (m, 1H); 1.29 (br d, J=5 Hz, 3H). Mass spectrum 457.6 (ESI, M+1). The enantiomers of the title compound were separated on HPLC (Chiralcel OJ column; 85:15 hexane:EtOH system).

Provenance & Evidence