Dichloromethane → Methyl 2-(4-benzyl-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

To a cooled (0° C.) solution of anhydrous zinc chloride (0.060 mg; 0.439 mmol) in tetrahydrofuran (0.8 mL) under nitrogen atmosphere was added dropwise a benzylmagnesium chloride solution (1M in THF) (0.408 mL; 0.408 mmol). After 15 min, the solution was allowed to warm up to room temperature for 10 min. To an argon purged reaction tube was added methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.100 g; 0.314 mmol), (1,1′-Bis(diphenylphosphino)ferrocene)-dichloropalladium(II) complex with dichloromethane (0.015 g; 0.022 mmol) and tetrahydrofuran (3 mL). The milky benzylzinc solution was added dropwise, the mixture was stirred at room temperature for 30 min and then heated at 65° C. for 20 h. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organics were washed with a solution of ethylenediaminetetraacetic acid, water, brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane furnished 0.095 g (81%) of the title compound as a colorless oil.

1. customTo an argon purged
2. customreaction tube
3. temperatureheated at 65° C. for 20 h
4. extractionextracted twice with ethyl acetate
5. washThe combined organics were washed with a solution of ethylenediaminetetraacetic acid, water, brine
6. dry with materialdried over magnesium sulphate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane

ORD-Eintrag

ord-789809e2357a4717ac63d8427475968c

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08906906B2