Dimethyl Sulfoxide → 5-Bromo-1-isopropylpyrimidin-2(1H)-one

Temperature

15 °C

With cooling with ice, potassium carbonate (17 g, 123 mmol) and isopropyl iodide (4.56 mL, 45.7 mmol) were added to a dimethyl sulfoxide (150 mL) solution of 5-bromo-2-hydroxypyrimidine hydrobromide (9.0 g, 35.2 mmol), and stirred at 15° C. for 16 hours. Water was added to the reaction mixture, and extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, hexane/ethyl acetate=3/2) to obtain the entitled compound (2.34 g, 31%) as a colorless solid.

1. extractionextracted three times with ethyl acetate
2. washThe organic layer was washed with saturated brine
3. dry with materialdried with anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. washThe organic layer was washed with saturated brine
6. dry with materialdried with anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified through silica gel column chromatography (C-300, hexane/ethyl acetate=3/2)

ORD record

ord-c130aeaad3354bfd960c09f322fa1bc2

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158652B2