Dimethylacetamide → 6-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile

온도

100 °C

Zinc (64 mg), 2-(di-tert-butylphosphino)biphenyl (163 mg), zinc cyanide (230 mg), and palladium (II) trifluoroacetate (81 mg) were added to a DMAc (16.5 mL) solution of 2-chloro-6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine (1.1 g) at room temperature in an argon atmosphere, and the mixture was stirred at 100° C. for 3 hours. After the reaction mixture was cooled to room temperature, water was added thereto, then extraction thereof was performed using EtOAc, and the extract was washed with water. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=1:1 to 1:4), whereby a mixture of 6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine-2-carbonitrile and 6-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile (502 mg) was obtained.

1. temperatureAfter the reaction mixture was cooled to room temperature
2. extractionextraction
3. washthe extract was washed with water
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=1:1 to 1:4), whereby
8. additiona mixture of 6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine-2-carbonitrile

ORD 기록

ord-9ae48241993d4c53bf1f34d515d62172

출처 데이터셋

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09328118B2