Trifluoroacetic acid → 1463484-29-8

Temperature

65 °C

To a solution of 5-fluoro-2-chloropyrimidine (500 μL, 5.24 mmol) in methanol (50 mL) is added benzoyl peroxide (1.5 g, 6.0 mmol) and trifluoroacetic acid (450 μL, 5.95 mmol). The resulting colorless clear solution is degassed by bubbling nitrogen through for 5 minutes and it is then heated at 65° C. for 18.5 hours. The solution is then cooled and concentrated. The resulting residue is diluted with chloroform (50 mL) and washed with saturated aqueous sodium bicarbonate solution (50 mL) and the layers are separated. The aqueous layer is re-extracted with chloroform (50 mL). The combined organic layers are dried over magnesium sulfate, filtered and concentrated to dryness under reduced vacuum. The residue is purified by flash silica gel column chromatography, eluting with gradient of ethyl acetate/dichloromethane (0% to 30%) to give the title compound (210 mg, 25%). 1H-NMR (CDCl3): δ (ppm) 8.42 (s, 1H), 4.85 (s, 2H), 3.57 (br, 1H).

1. customThe resulting colorless clear solution is degassed
2. customby bubbling nitrogen through for 5 minutes and it
3. temperatureThe solution is then cooled
4. concentrationconcentrated
5. additionThe resulting residue is diluted with chloroform (50 mL)
6. washwashed with saturated aqueous sodium bicarbonate solution (50 mL)
7. customthe layers are separated
8. extractionThe aqueous layer is re-extracted with chloroform (50 mL)
9. dry with materialThe combined organic layers are dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated to dryness under reduced vacuum
12. customThe residue is purified by flash silica gel column chromatography
13. washeluting with gradient of ethyl acetate/dichloromethane (0% to 30%)

ORD record

ord-8cf1dd45781546a6bf3f2e1a6f5acecc

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772282B2