1-(2-(2-bromoethoxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole → N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methyl-N2-(2-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)ethyl)ethane-1,2-diamine

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 (0.2 g, 0.623 mmol) in DMF (3 mL) was added TEA (0.095 g, 0.935 mmol) followed by 1-(2-(2-bromoethoxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (Preparation J, 0.245 g, 0.233 mmol) at room temperature. The reaction mixture was stirred at rt for 18 h. The solvent was removed under reduced pressure and the residue was dissolved 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, with 10% methanol in chloroform) to get N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methyl-N2-(2-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)ethyl)ethane-1,2-diamine (0.04 g, 13.12%) as a dark brown solid. LC-MS (M+H)+=567.2. 1H NMR (400 MHz, CDCl3) δ ppm 8.25 (1H, s), 7.14-7.08 (3H, m), 6.99-6.95 (2H, m), 6.41 (1H, s), 6.32 (1H, d, J=8.4 Hz), 4.39 (2H, br s), 4.14 (1H, t, J=8.8 Hz), 3.93-3.88 (4H, m), 3.22-3.09 (6H, m), 2.55-2.54 (1H, m), 2.46 (3H, s), 1.99-1.98 (1H, m).

Provenance & Evidence