反应详情

Next, 2.01 g of 4-tert-butyl-6-chloropyrimidine obtained in Step 2, 3.63 g of 3,5-dimethylphenylboronic acid, 2.48 g of sodium carbonate, 0.10 g of bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of DMF were put into a recovery flask equipped with a reflux pipe, and the mixture was bubbled with argon for 15 minutes. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes to be heated. Here, into the flask were further put 0.90 g of 3,5-dimethylphenylboronic acid, 0.64 g of sodium carbonate, and 0.025 g of Pd(PPh3)2Cl2, and the mixture was bubbled with argon for 15 minutes. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) again for 60 minutes to be heated. Then, water was added to this solution and the 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 the obtained residue was purified by silica gel column chromatography using dichloromethane and ethyl acetate as a developing solvent in a ratio of 10:1, so that HtBudmppm (abbreviation), which was the pyrimidine derivative to be produced, was obtained as a pale yellow oil in a yield of 96%. Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). A synthesis scheme of Step 3 is shown in (k-3).

1. customequipped with a reflux pipe
2. customthe mixture was bubbled with argon for 15 minutes
3. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes
4. temperatureto be heated
5. customthe mixture was bubbled with argon for 15 minutes
6. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) again for 60 minutes
7. temperatureto be heated
8. additionThen, water was added to this solution
9. extractionthe organic layer was extracted with dichloromethane
10. washThe obtained organic layer was washed with water and saturated brine
11. dry with materialwas dried with magnesium sulfate
12. filtrationAfter the drying, the solution was filtered
13. distillationThe solvent of this solution was distilled off
14. customthe obtained residue was purified by silica gel column chromatography
15. customto be produced
16. customwas obtained as a pale yellow oil in a yield of 96%
17. customNote that the irradiation with microwaves
18. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
19. customA synthesis scheme of Step 3