Diisopropylethylamine → 5-Bromo-3-nitro-4-(4-(1-phenylethyl)piperazin-1-yl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-amino-5-bromo-4-chloro-3-nitropyridine (0.252 g, 1.00 mmol) and isopropanol (18 ml) was added 1-(1-phenylethyl)piperazine (0.209 g, 1.10 mmol) followed by diisopropylethylamine (0.20 ml, 1.15 mmol). The reaction mixture was stirred at 45° C. for 20 h, then allowed to cool to room temperature and diluted with isopropanol (10 ml). The resulting precipitate was collected by filtration, washed with isopropanol (3×5 ml), diethyl ether (3×5 ml), and dried. The title compound was obtained as a yellow solid (0.300 g, 74%). 1H-NMR (500 MHz, DMSO-d6) 1.30 (d, J=6.7 Hz, 3H, CHCH3), 2.42 (m, 2H) and 2.54 (m, 2H) (piperazine N(CH2)2), 3.03 (br s, 4H, piperazine N(CH2)2), 3.45 (q, J=6.7 Hz, 1H, CHCH3), 6.95 (s, 2H, NH2), 7.23 (m, 1H) and 7.32 (m, 4H) (PhH), 8.13 (s, 1H, pyridine 6-H);

Provenance & Evidence