2-(2-Bromoethoxy)-4-nitrobenzonitrile → 2-(2-((2-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)ethyl)(methyl)amino)ethoxy)-4-nitrobenzonitrile

Participants

Reaction Steps

To a solution of N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methylethane-1,2-diamine {Preparation Sd Step (1), 0.5 g, 1.56 mmol} in DMF (5 mL) was added TEA (0.234 g, 2.34 mmol) followed by 2-(2-bromoethoxy)-4-nitrobenzonitrile (0.423 g, 1.56 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was taken in dichloromethane (5 mL) and silica (1 g). The resultant slurry of the compound in silica was subjected to flash chromatography using a Teledyne Isco instrument (12 g RediSep silica column, 10% methanol in chloroform) to get 2-(2-((2-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)ethyl)(methyl)amino)ethoxy)-4-nitrobenzonitrile (0.3 g, 37.68%) as a dark brown solid. LC-MS (M+H)+=511.2. 1H NMR (400 MHz, CDCl3) δ ppm 7.91-7.89 (1H, m), 7.85 (1H, s), 7.72-7.70 (1H, m), 7.14-7.10 (2H, m), 6.98-6.96 (2H, m), 4.42-4.39 (2H, m), 4.17-4.15 (1H, m), 3.66-3.56 (2H, m), 3.49 (3H, s), 3.35-3.26 (2H, m), 3.18-3.12 (4H, m), 2.78-2.63 (1H, m), 1.99-1.98 (1H, m).

Provenance & Evidence