反应详情

温度

75 °C

To a 10 mL round bottomed flask was added 5-bromo-1-(2-hydroxyethyl)pyrimidin-2(1H)-one (0.088 g, 0.40 mmol), phenylboronic acid (0.098 g, 0.80 mmol), 1,2-dimethoxyethane (2.5 mL) and 2 M sodium carbonate (0.40 mL, 0.80 mmol). The mixture was carefully evacuated and backfilled with N2. This was repeated twice. To the mixture was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II)dichloromethane adduct (0.029 g, 0.040 mmol). The mixture was again carefully evacuated and backfilled with N2. This was repeated once. The mixture was then heated at 75° C. for 1.5 hours. After cooling to room temperature, the mixture was poured into water (50 mL) and then extracted with EtOAc (2×) and then with 25% iPrOH/CHCl3 (3×). The combined extracts were washed with brine (1×), dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (0 to 2% MeOH (2M NH3)/CH2Cl2) afforded 1-(2-hydroxyethyl)-5-phenylpyrimidin-2(1H)-one (0.061 g, 70% yield) as an off-white solid. MS (ESI, pos. ion.) m/z: 217 (MH+). Calc'd exact mass for C12H12N2O2: 216. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.71 (q, J=5.3 Hz, 2 H), 4.00 (t, J=5.3 Hz, 2 H), 4.95 (t, J=5.6 Hz, 1 H), 7.35 (t, J=7.3 Hz, 1 H), 7.46 (t, J=7.6 Hz, 2 H), 7.61 (d, J=7.4 Hz, 2 H), 8.44 (d, J=3.3 Hz, 1 H), 8.95 (d, J=3.3 Hz, 1 H).

1. customThe mixture was carefully evacuated
2. customThe mixture was again carefully evacuated
3. temperatureAfter cooling to room temperature
4. additionthe mixture was poured into water (50 mL)
5. extractionextracted with EtOAc (2×)
6. washThe combined extracts were washed with brine (1×)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated onto silica
9. customPurification by silica gel chromatography (0 to 2% MeOH (2M NH3)/CH2Cl2)