1,2-Dimethoxyethane → 2-(2-chlorophenyl)-6-(5-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one

온도

100 °C

6-Bromo-2-(2-chlorophenyl)thieno[3.2-d]pyrimidin-4(3H)-one (157 mg), tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (425 mg), sodium carbonate (138 mg), 1,2-dimethoxyethane (4.0 mL) and water (2.0 mL) were placed in a flask, and the atmosphere in the flask was purged with argon. [1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane complex (1:1) (38 mg) was added, and the atmosphere in the flask was purged again with argon. The reaction system was stirred at 100° C. for 1 hr, 8M aqueous sodium hydroxide solution (1 mL) was added, and the mixture was stirred at 100° C. for 30 min. After stirring, the mixture was extracted with ethyl acetate/tetrahydrofuran mixture, and the extract was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained pale-yellow solid was crystallized from methanol/ethyl acetate to give the title compound (43 mg) as a yellow solid.

1. customthe atmosphere in the flask was purged with argon
2. addition[1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane complex (1:1) (38 mg) was added
3. customthe atmosphere in the flask was purged again with argon
4. addition8M aqueous sodium hydroxide solution (1 mL) was added
5. stirringthe mixture was stirred at 100° C. for 30 min
6. stirringAfter stirring
7. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran mixture
8. concentrationthe extract was concentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
10. customthe obtained pale-yellow solid was crystallized from methanol/ethyl acetate

ORD 기록

ord-fb8dfb4495cd4da4aba56a3e1163e554

출처 데이터셋

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08722660B2