Sodium Carbonate → 5-Bromo-2-phenylpyrimidine

To a degassed solution of phenylboronic acid (8.93 g, 73.22 mmol, 1.0 equiv; commercially available), 5-bromo-2-iodo-pyrimidine (20.86 g, 73.22 mmol, 1.0 equiv; commercially available) and tetrakis(triphenylphosphine) palladium(0) (0.85 g, 0.73 mmol, 0.01 equiv) in toluene (180 mL) was added Na2CO3 (15.52 g, 146.45 mmol, 2.0 equiv), dissolved in water (60 mL), and the reaction mixture heated to reflux. After 18 h, tetrakis(triphenylphosphine) palladium(0) (0.42 g, 0.37 mmol, 0.005 equiv) was added and the reaction mixture heated for an additional time period of 24 h. The solvent was removed under reduced pressure and the crude reaction product extracted from a sat. solution of NaCl (200 mL) with ethyl acetate (3×150 mL). The combined organic phases were dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude material purified by silica column chromatography eluting with heptane/ethyl acetate (9:1) to provide 8.60 g (50%) of the title compound.

1. temperaturethe reaction mixture heated to reflux
2. temperaturethe reaction mixture heated for an additional time period of 24 h
3. customThe solvent was removed under reduced pressure
4. customthe crude reaction product
5. extractionextracted from a sat. solution of NaCl (200 mL) with ethyl acetate (3×150 mL)
6. dry with materialThe combined organic phases were dried over Na2SO4
7. concentrationconcentrated by evaporation under reduced pressure
8. customthe crude material purified by silica column chromatography
9. washeluting with heptane/ethyl acetate (9:1)

ORD record

ord-4055d3cb42da40dc90792202b19ebb1a

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07939661B2