反应详情

温度

110 °C

3-Hydroxybenzyl alcohol (1.50 g, 12.1 mmol) and 2-chloro-5-bromopyrimidine (2.57 g, 13.3 mmol) were suspended in DMSO (20 mL), treated with cesium carbonate (4.35 g, 13.4 mmol) and heated to 110° C. After 16 h, the reaction mixture was cooled and partitioned between water (200 mL) and heptane:ethyl acetate (1:1, 200 mL). The organic layer was separated and the aqueous was extracted again with heptane:ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica (20-70% EtOAc:heptane) to afford the title compound (0.790 g, 23% yield) as a light yellow oil. MS (APCI) M+1=281.0; 1H NMR (400 MHz, CDCl3) δ ppm 4.74 (s, 2H) 7.08-7.14 (m, 1H) 7.20-7.23 (m, 1H) 7.25-7.30 (m, 1H) 7.43 (t, J=7.80 Hz, 1H) 8.57 (s, 2H).

1. temperaturethe reaction mixture was cooled
2. custompartitioned between water (200 mL) and heptane:ethyl acetate (1:1, 200 mL)
3. customThe organic layer was separated
4. extractionthe aqueous was extracted again with heptane
5. dry with materialThe combined organic layers were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography on silica (20-70% EtOAc:heptane)