Triethylamine → 4-(2,2-Dimethyl-propylamino)-5-[3-(4-pyridin-2-yl-piperazin-1-yl)-prop-1-ynyl]-pyrimidine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

1-(2-Propynyl)-4-(2-pyridinyl)-piperazine (prepared from 1-(2-pyridinyl)-piperazine and propargyl bromide) (1.5 mmol) is dissolved in DMF at room temperature under nitrogen atmosphere. To the solution, 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (1 mmol), triethylamine (3 mmol), copper(I) iodide (0.1 mmol), and dichlorobis(triphenylphosphine)palladium(II) (0.05 mmol) are added successively. The mixture is heated at 80° C. under nitrogen atmosphere for 3 h. After cooling at room temperature, the mixture is diluted with H2O and extracted with AcOEt. The organic layer is dried over magnesium sulfate and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane:AcOEt=1:5) to give 4-(2,2-dimethyl-propylamino)-5-[3-(4-pyridin-2-yl-piperazin-1-yl)-prop-1-ynyl]-pyrimidine-2-carbonitrile. Yield 97%. Rf=0.30 (n-hexane:AcOEt=1:5). 1H NMR (400 MHz, CDCl3) δ 0.95(s, 9H), 2.75-2.73(m, 4H), 3.36(d, 2H), 3.63-3.60(m, 4H), 3.69(s, 2H), 5.78(brs, 1H), 6.63-6.67(m, 2H), 7.47-7.52(m, 1H), 8.19-8.21(m, 2H).

Provenance & Evidence