反应详情

温度

100 °C

A suspension of 2-(benzylamino)-5-bromo-3-methylpyrimidin-4(3H)-one (0.130 g, 0.442 mmol), 4-(benzyloxy)-3-fluorophenylboronic acid (0.130 g, 0.530 mmol), Pd(PPh3)4 (0.026 g, 0.022 mmol) and lithium chloride (0.075 g, 1.77 mmol) in dioxane (2 mL) and 2M aqueous Na2CO3 (2 mL) was stirred at 100° C. for 1 hour. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with 10:1 CH2Cl2/EtOAc. The product was obtained (146 mg; 80%) as an off-white foam solid. 1H NMR (400 MHz, DMSO-d6) δ 7.89 (s, 1H), 7.55 (dd, 1H), 7.48-7.43 (m, 2H), 7.43-7.29 (m, 8H), 7.26-7.15 (m, 2H), 5.18 (s, 2H), 4.62 (d, 2H), 3.42 (s, 3H). LRMS (APCI pos) m/e 416 (M+1).

1. temperatureThe reaction mixture was cooled to room temperature
2. custompartitioned between EtOAc and H2O
3. customThe layers were separated
4. extractionthe aqueous layer was re-extracted with EtOAc (1×)
5. dry with materialThe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by flash column chromatography
9. washeluting with 10:1 CH2Cl2/EtOAc
10. customThe product was obtained (146 mg; 80%) as an off-white foam solid