Hydrochloric Acid → HCID 178463886, compound

Participants

Reaction Steps

To a mixture of 1-(N-pyrrolyl)-1-phenyl ethylene (2.0 g, 11.5 mmol) [freshly prepared through TiCl4 mediated condensation between acetophenone (Aldrich Chemical Company) and pyrrolidine (Aldrich Chemical Company) (1.70 g, 8.76 mmol) in ether by the method described by Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5782-5789)] and Et3N (1.7 mL, 12.2 mmol) in CH2Cl2 (15 mL) at room temperature was added 4,6-dichloro-5-nitro pyrimidine (Aldrich Chemical Company) (1.6 g, 8.2 mmol) slowly under a stream of N2. The reaction mixture became hot upon mixing and the solution was stirred at room temperature for 2.5 h. The solution was concentrated and the residue was treated with hot toluene, filtered, washed with hot toluene (3×), and the filtrate was concentrated in vacuo. Half of this material was dissolved in toluene (10 mL), and Et3N (2.0 mL) followed by Et2NH (Aldrich Chemical Company) (2.0 mL, 20 mmol) were added slowly, leading to an exothermic reaction. The mixture was stirred at 100° C. (sand bath temperature) overnight, cooled under a N2 stream, and partitioned between H2O and EtOAc. The organic layer was concentrated in vacuo. The residue was dissolved in i-PrOH-MeOH (5:1, ˜20 mL) and hydrogenated with 10% Pd/C (0.5 g) and PtO2 (0.1 g) as catalysts for 4 d at room temperature and atmospheric pressure. The solution was filtered through a plug of celite and concentrated with a rotary evaporator. The residue was purified by flash chromatography on silica gel with a gradient eluant of i-PrOH (0.4 to 5%):CH2Cl2 (99.6 to 95%) to afford the free base which was treated with 1N ethereal HCl to give 0.035 g (3.0%) of the title compound as a yellow solid. MS m/z+267 (M+1); m/z−265 (M−1). 1H NMR (CD3OD; 500 MHz): δ 1.46 (t, 6, J=7.0), 4.26 (q, 4, J=7.0),. 7.61 (m, 3), 7.23 (s, 1), 8.30 (s, 1), 7.73 (m, 2). HRMS: Calcd for M+H, C16H19N4: 267.1606. Found: 267.1598.

Provenance & Evidence