Imidazole → Pyrimidine, 2-(1,1-difluoro-2-iodoethyl)-

Temperature

0 °C

A homogeneous solution of 2,2-difluoro-2-pyrimidin-2-yl-ethanol (689 mg, 4.31 mmol), as prepared in the previous step, PPh3 (1.69 g, 6.44 mmol), and imidazole (590 mg, 8.67 mmol) in toluene (5.8 mL) and CH3CN (2.9 mL) was stirred at 0° C. for 5 min, and was then treated with I2 (1.61 g, 6.34 mmol) in two portions and stirred at 0° C. for another 5 min. The resulting brown opaque slurry was then heated at 90° C. for 19 h, and then allowed to cool to rt. The mixture was filtered, the beige filter cake was washed with toluene (3×10 mL), and the combined brown filtrates were concentrated. Silica flash chromatography of the residue (2:1 hex/EtOAc eluent) afforded the title compound as a pale yellow oil (849 mg, 73%).

1. stirringstirred at 0° C. for another 5 min
2. temperatureThe resulting brown opaque slurry was then heated at 90° C. for 19 h
3. temperatureto cool to rt
4. filtrationThe mixture was filtered
5. washthe beige filter cake was washed with toluene (3×10 mL)
6. concentrationthe combined brown filtrates were concentrated

ORD record

ord-2a5d9b66031e426f860c36afcf83578d

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829584B2