(Trifluoromethyl)trimethylsilane → HCID 59526148, compound

Temperature

0 °C

4-Chloropyrimidine-2-carbaldehyde (283 mg, 1.99 mmol) was dissolved in tetrahydrofuran (11.4 mL) and cooled to 0° C. Trimethyl(trifluoromethyl)silane (0.37 mL, 2.38 mmol) was added followed by 1 M tetra-n-butylammonium fluoride in tetrahydrofuran (2.38 mL, 2.38 mmol). The ice bath was removed and the reaction was stirred for 1 hour. The reaction was then diluted with water and brine and extracted with ethyl acetate three times. The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting mixture was purified via silica gel chromatography (0-5% methanol in ethyl acetate) to afford the title compound.

1. customThe ice bath was removed
2. additionThe reaction was then diluted with water and brine
3. extractionextracted with ethyl acetate three times
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe resulting mixture was purified via silica gel chromatography (0-5% methanol in ethyl acetate)

ORD record

ord-ee823a748f3a4ede815d85be277910a7

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2