Water → HCID 24901907, compound

Temperature

90 °C

To a sealed tube was added 2,4-dichloropyrimidine (100 mg, 0.671 mmol), 4-(trifluoromethoxy)phenylboronic acid (138 mg, 0.671 mmol), tetrakis(triphenylphosphine)palladium0) (78 mg, 0.067 mmol), acetonitrile (2 mL) and 2M Na2CO3 in H2O (1.007 mL, 2.014 mmol). Argon was bubbled through the reaction mixture for 1 min. The reaction mixture was then sealed and stirred at 90° C. for 16 hrs. The reaction was cooled to rt and diluted with EtOAc (30 ml). The resulting organic solution was washed with water (30 ml) and saturated aqueous NaCl (30 ml). The organic layer was dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-40% EtOAc/Hex to give the product, 2-chloro-4-(4-(trifluoromethoxy)phenyl)pyrimidine, (62 mg, 0.226 mmol, 33.6% yield) as a white solid. Anal. Calcd. for C11H6ClF3N2O m/z 273.9, found: 275.0 (M+H)+.

1. customArgon was bubbled through the reaction mixture for 1 min
2. customThe reaction mixture was then sealed
3. temperatureThe reaction was cooled to rt
4. additiondiluted with EtOAc (30 ml)
5. washThe resulting organic solution was washed with water (30 ml) and saturated aqueous NaCl (30 ml)
6. dry with materialThe organic layer was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe resulting residue was purified
10. washeluting with a gradient of 0-40% EtOAc/Hex

ORD record

ord-8816b8dd7e79470aba55f6b0acb51fd3

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815909B2