反应详情

A solution of 2-benzyl-5-bromopyrimidin-4(3H)-one (0.300 g, 1.13 mmol), 4-(benzyloxy)-3-fluorophenylboronic acid (0.334 g, 1.36 mmol), Pd(PPh3)4 (0.065 g, 0.057 mmol) and lithium chloride (0.240 g, 5.66 mmol) in dioxane (3 mL) and 2 M aq Na2CO3 (0.3 mL) was stirred at 100° C. for 18 hours. The reaction mixture was partitioned between EtOAc and H2O. The phases were separated, and the aqueous phase was re-extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude dark yellow solid. Purification of the crude product was achieved by trituration with dichloromethane. The resulting solid was filtered, washed with dichloromethane, collected and dried under vacuum. The filtrate was concentrated and the trituration procedure was repeated (2×) with EtOAc. The solids were combined to yield the desired product (0.284 g, 65%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.93 (br s, 1H), 8.13 (s, 1H), 7.66 (dd, J=2.3, 13.3 Hz, 1H), 7.53-7.22 (s, 12H), 5.21 (s, 2H), 3.90 (s, 2H). LRMS (APCI pos) m/e 387 (M+1).

1. customThe reaction mixture was partitioned between EtOAc and H2O
2. customThe phases were separated
3. extractionthe aqueous phase was re-extracted with EtOAc (3×)
4. dry with materialThe combined organic layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customto yield a crude dark yellow solid
8. customPurification of the crude product
9. filtrationThe resulting solid was filtered
10. washwashed with dichloromethane
11. customcollected
12. customdried under vacuum
13. concentrationThe filtrate was concentrated