Toluene → HCID 65645365, compound

Temperature

100 °C

To a stirred solution of 4,6-dichloro-5-methylpyrimidine (1 g, 6.13 mmol) in toluene (38.2 ml) was added potassium cyclopropyl(trifluoro)borate (0.999 g, 6.75 mmol), di(1-adamantyl)-n-butylphosphine (0.066 g, 0.184 mmol), palladium(II) acetate (0.028 g, 0.123 mmol), cesium carbonate (6.00 g, 18.40 mmol) and the reaction mixture stirred under argon at 100° C. for 24 hours. The reaction mixture was washed with water and extracted with ethyl acetate (3×25 mL). The organic layers were collected, dried under magnesium sulphate and evaporated under reduced pressure. Crude residues were purified by Si SP4 column chromatography eluting with a gradient of 0-15% ethyl acetate-isohexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a white solid (491 mg);

1. washThe reaction mixture was washed with water
2. extractionextracted with ethyl acetate (3×25 mL)
3. customThe organic layers were collected
4. customdried under magnesium sulphate
5. customevaporated under reduced pressure
6. customCrude residues were purified by Si SP4 column chromatography
7. washeluting with a gradient of 0-15% ethyl acetate-isohexane
8. additionProduct containing fractions
9. customevaporated under reduced pressure

ORD record

ord-dc36c53046b74c13ae711bfa0f9d9a85

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796283B2