反应详情

温度

90 °C

Sodium (25 wt % dispersion in paraffin wax, 0.10 g, 3.8 mmol) was added to t-butanol (1.8 mL) at rt. After 10 minutes, a solution of 4-[cyclohexyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (1.0 g, 2.5 mmol) in 10 mL of toluene was added to the sodium t-butoxide solution and the resulting mixture was heated at 90° C. for 30 minutes. The reaction mixture was then cooled and the solution was adjusted to pH 7 using a 1N HCl solution. The solution was then extracted with EtOAc (2×20 mL) and the organic layer was dried (MgSO4) and concentrated to provide 0.55 g, (42%) of the title compound. 1H NMR indicated the presence of both enol and keto forms in a 1:1.75 ratio. 1H-NMR (400 MHz, CDCl3) δ ppm 8.63 (s, 1H), 8.18 (s, 1H), 4.76-4.82 (m), 4.58-4.68 (m), 4.16-4.36 (m), 3.91-3.96 (m), 3.60-3.64 (m), 3.46-3.49 (m), 2.53 (s, 3H), 2.50 (s, 5.25H), 1.86-1.89 (m), 1.71-1.73 (m), 1.32-1.56 (m), 1.26 (t, J=7.2 Hz), 1.10-1.21 (m).

1. temperatureThe reaction mixture was then cooled
2. extractionThe solution was then extracted with EtOAc (2×20 mL)
3. dry with materialthe organic layer was dried (MgSO4)
4. concentrationconcentrated