33.24% |
With N-ethyl-N,N-diisopropylamine; In ethanol; for 2.5h;Reflux; |
A mixture of 5 (0.10g, 0.48mmol), DIPEA (0.08ml, 0.48mmol) and EtOH (5ml) was mixed with the 85 (0.07g, 0.48mmol) and refluxed for 2.5hrs. The reaction was quenched by saturated NaHCO3 (aq.) and the mixture was extracted by ethyl acetate (30ml x 3). The residue was purified by flash column over silica gel (dichloromethane: methanol = 9: 1, Rf = 0.28) to afford 89 (0.05g, 33.24%) as a pale yellow solid. 1H-NMR (300MHz, CDCl3): delta 1.13 (t, J= 7.2 Hz, 3H), 2.46 (q, J= 7.2 Hz, 2H), 2.62 (t, J= 5.1 Hz, 4H), 2.98 (d, J= 5.1 Hz, 3H), 3.19 (t, J= 5.1 Hz, 4H), 5.17-5.29 (m, 1H), 5.55 (br, 1H), 6.91 (d, J= 8.7 Hz, 2H), 7.37 (d, J= 8.1 Hz, 1H), 7.46 (s, 1H), 8.20 (d, J= 44.7 Hz, 1H). |
|
With N-ethyl-N,N-diisopropylamine; sodium iodide; In ethanol; at 80℃; for 3h; |
A mixture of (4-chloro-[1,3,5]triazin-2-yl)-methyl-amine (290 mg, 2.00 mmol), Nal (28 mg)and <strong>[115619-01-7]4-(4-ethylpiperazin-1-yl)-aniline</strong> (410 mg, 2.0 mmol) in EtOH (20 ml) and N-ethyl-diisopropyl amine (350 ul, 2.0 mmol) is heated to 80C for 3 h under a nitrogen atmosphere.The reaction mixture is cooled to RT, concentrated partially in vacuo and diluted with hexaneat 0 C. The precipitate is filtered off, washed with Et2O and re-dissolved in EE and water.The separated off aqueous phase is extracted twice with EE, the organic layer washed withwater and brine, dried (Na2SO4) and concentrated, yielding the title compound: ESI-MS: 314[MH]*; TLC: Rf = 0.10 (DCM/MeOH 9:1). |