N,N,N',N'-Tetramethylethylenediamine → 1-(4-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenyl)-4-(phenylethynyl)pyrimidin-2(1H)-one

Participants

Reaction Steps

To a stirred mixture of 4-(phenylethynyl)pyrimidin-2(1H)-one Part B (20 mg, 0.1 mmol), 4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acid Part D (48.9 mg, 0.2 mmol), and copper (II) acetate (18.5 mg, 0.1 mmol) in MeOH (2 mL) and H2O (0.5 mL) was added N1,N1,N2,N2-tetramethylethane-1,2-diamine (24 mg, 0.2 mmol) at RT. The reaction mixture was stirred at RT for 45 min under oxygen, diluted with CH2Cl2, washed sequentially with 5% aq. H2SO4 and sat. NaHCO3. The organic phase was dried (MgSO4), concentrated, and the residue was subjected to flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient) to afford impure product. Trituration with methyl t-butyl ether yielded the title compound B-1 (15 mg, 0.038 mmol, 37% yield) as a pure solid. LC/MS 391 (M+H)+, tR 0.82 min (method 5); 1H NMR (400 MHz, chloroform-D) δ 7.70 (1H, d, J=6.78 Hz), 7.51-7.66 (2H, m), 7.37-7.47 (3H, m), 6.95-7.12 (2H, m), 6.90 (1H, dd, J=8.53, 2.51 Hz), 6.54 (1H, d, J=6.78 Hz), 3.88 (3H, s), 3.85 (2H, s), 1.36 (6H, s).

Provenance & Evidence