Pyridine → 4'-{[4-Butyl-1-(3-hydroxyphenyl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile

To a suspension of 4′-[(4-butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (5.0 g), (3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)boronic acid (9.0 g), triethylamine (10.0 mL), pyridine (5.0 mL) and molecular sieves 4 A (10.0 g) in methylene chloride (100 mL) was added copper(II) acetate (5.0 g), and the mixture was stirred for 2 days. The reaction mixture was diluted with ethyl acetate. The insoluble material was filtered off through celite, and the filtrate was concentrated. The residue was dissolved in tetrahydrofuran (20 mL), tetrabutylammonium fluoride (1.7 g) was added, and the mixture was stirred for 15 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (1.71 g, 21%).

1. filtrationThe insoluble material was filtered off through celite
2. concentrationthe filtrate was concentrated
3. dissolutionThe residue was dissolved in tetrahydrofuran (20 mL)
4. additiontetrabutylammonium fluoride (1.7 g) was added
5. stirringthe mixture was stirred for 15 hr
6. additionEthyl acetate and water were added to the reaction mixture
7. extractionthe mixture was extracted with ethyl acetate
8. washThe organic layer was washed with saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customthe solvent was evaporated
11. customThe residue was purified by silica gel column chromatography

ORD 기록

ord-021dcd6b1c7e47c39edd527294cd9737

출처 데이터셋

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07998968B2