Trifluoroacetic acid → 5-Chloro-3-nitro-4-(4-(pyrimidin-5-ylmethyl)piperazin-1-yl)pyridin-2-amine

Participants

Reaction Steps

This was prepared using the same procedure as for 5-bromo-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amine, but here using tert-butyl 4-(pyrimidin-5-ylmethyl)piperazine-1-carboxylate (1.1 eq, 0.13 mmol, 35 mg), TFA (0.25 mL) and CH2Cl2 (1 mL), then 4,5-dichloro-3-nitropyridin-2-amine (37 mg, 0.11 mmol) in iPrOH (1 mL) and DIPEA (0.25 mL). Filtration and washing as previously described gave the product (22 mg, 50% for two steps) as a yellow solid; δH (500 MHz, DMSO-d6) 2.52 (s, br, 4H, piperazine N(CH2)2), 3.07 (t, J=4.5 Hz, 4H, piperazine N(CH2)2), 3.60 (s, 2H, CH2), 6.95 (s, br, 2H, NH2), 8.06 (s, 1H, pyridine H-6), 8.75 (s, 2H, pyrimidine H-4 & H-6), 9.10 (s, 1H, pyrimidine H-2);

Provenance & Evidence