Triethylamine → HCID 178428298, compound

Participants

Reaction Steps

To a solution of 4,6-dichloro-5-nitro-2-[(E)-2-phenylvinyl]pyrimidine (200 mg, 0.676 mmol) in THF (5 mL) was added triethylamine (204 mg, 2.03 mmol) and the reaction mixture was stirred for 15 minutes. 3-Amino-5-methyl-pyrazole (66 mg, 0.68 mmol) in THF (3 mL) was added dropwise to the reaction mixture. After 1 hour, N-methylpiperazine (74 mg, 0.74 mmol) in THF (3 mL) was added to the reaction mixture dropwise. The reaction mixture was stirred at room temperature for 1 hour followed by addition of water (10 mL). After stirring for 15 minutes, ethyl acetate (50 mL) was added. The organic layer was separated, dried and the solvent evaporated under reduced pressure. The residue was triturated with chloroform and hexane to obtain 6-(4-methylpiperazin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-5-nitro-2-[(E)-2-phenylvinyl]pyrimidin-4-amine (80 mg). 1H NMR (400 MHz, DMSO-d6): δ 12.35 (br, 1H), 10.52 (br, 1H), 7.95 (d, 1H, J=16 Hz), 7.83 (d, 2H, J=6.8 Hz), 7.5 (m, 3H), 7.11 (d, 1H, J=16 Hz), 6.8 (s, 1H), 3.65 (br, 4H), 2.5 (br, 4H), 2.36 (s, 3H), 2.29 (s, 3H). MS (m/z) 421 (M+1).

Provenance & Evidence