反应详情

To a mixture of 4,4,5,5-tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane (0.936 g, 2.7 mmol), Pd(dppf)Cl2 (0.10 g, 0.14 mmol) in dioxane and Sodium carbonate (2.0 M in water, 2.7 ml, 5.5 mmol) was added 4-chloro-2-methylthiopyrimidine (0.38 ml, 3.3 mmol). The brown mixture was sealed and heated to 80 deg. C. overnight. In the morning the reaction was partitioned between EtOAc/1N NaOH. The aqueous layer was extracted once with EtOAc. The combined organics were dried over anhyd. Na2SO4, filtered, and concentrated to a brown oil. This material was treated with CH2Cl2 and purified by silica gel chromatography eluting with 0-25% EtOAc/hexane. The product-containing fractions were concentrated to afford 2-(methylthio)-4-(2-(4-nitrophenoxy)phenyl)pyrimidine as a clear oil. MS m/z=340 [M+1]+. Calc'd for C17H13N3O3: 339.37.

1. customThe brown mixture was sealed
2. temperatureheated to 80 deg. C
3. customovernight
4. customIn the morning the reaction was partitioned between EtOAc/1N NaOH
5. extractionThe aqueous layer was extracted once with EtOAc
6. customThe combined organics were dried over anhyd
7. filtrationNa2SO4, filtered
8. concentrationconcentrated to a brown oil
9. additionThis material was treated with CH2Cl2
10. custompurified by silica gel chromatography
11. washeluting with 0-25% EtOAc/hexane
12. concentrationThe product-containing fractions were concentrated