反应详情

First, 4.97 g of 4,6-dichloropyrimidine, 5.02 g of 2,5-dimethylphenylboronic acid, 3.55 g of sodium carbonate, 0.29 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of acetonitrile were put in a recovery flask equipped with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was heated by being irradiated with microwaves (2.45 GHz, 100 W) for 30 minutes. Further, 1.25 g of 2,5-dimethylphenylboronic acid, 0.89 g of sodium carbonate, and 0.073 g of Pd(PPh3)2Cl2 were put in the flask, and the reaction container was heated again by being irradiated with microwaves (2.45 GHz, 100 W) for 30 minutes. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and saturated brine, and was dried with magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by flash column chromatography using hexane and ethyl acetate in a ratio of 5:1 as a developing solvent, so that the target pyrimidine derivative was obtained (pale yellow oily substance, yield of 64%). A synthetic scheme of Step 1 is shown in (d-1) below.

1. customequipped with a reflux pipe
2. temperatureThis reaction container was heated
3. customby being irradiated with microwaves (2.45 GHz, 100 W) for 30 minutes
4. temperaturethe reaction container was heated again
5. customby being irradiated with microwaves (2.45 GHz, 100 W) for 30 minutes
6. extractionan organic layer was extracted with dichloromethane
7. washThe obtained organic layer was washed with water and saturated brine
8. dry with materialwas dried with magnesium sulfate
9. filtrationAfter the drying, the solution was filtered
10. distillationThe solvent of this solution was distilled off
11. customthe obtained residue was purified by flash column chromatography