Bromine → HCID 66977175, compound

Participants

Reaction Steps

To solution of ethyl 1-(5-(4-amino-3-nitrophenyl)pyrimidin-2-yl)-4-ethylpiperidine-4-carboxylate (6.0 g, 15.02 mmol) in acetic acid (60.0 mL) was added bromine (0.85 mL, 16.52 mmol) dropwise at rt and the mixture then stirred at rt for 16 h. After completion of reaction the mixture was poured into 100 mL of ice-cold water, extracted with EtOAc (3×150 mL) and the combined organic layer washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel column chromatography using 10% EtOAc:Hexane to obtain the product as a beige solid (5.60 g, 78%). 1H NMR (CDCl3): δ 8.66 (s, 2H), 8.18 (s, 2H), 7.21 (br s, 2H), 4.39-4.43 (m, 2H), 4.13-4.18 (m, 2H), 3.06-3.11 (m, 2H), 2.04-2.08 (m, 2H), 1.50-1.52 (m, 2H), 1.38-1.39 (m, 2H), 1.21 (t, J=7.60 Hz, 3H) and 0.75 (t, J=7.60 Hz, 3H). MS: 478.11 [M+H]+, 81%.

Provenance & Evidence