Borane;tetrahydrofuran → (2-(Trifluoromethyl)pyrimidin-5-yl)methanol

To an ice-bath cooled solution of 2-(trifluoromethyl)pyrimidine-5-carboxylic acid (Description 118; 2 g, 10.4 mmol) in anhydrous tetrahydrofuran (100 ml) was added dropwise borane tetrahydrofuran complex [1.0M solution in THF] (15.6 ml, 15.6 mmol), after complete addition the mixture was stirred at room temperature for 90 mins. The reaction was quenched by the careful addition of water (2 ml), followed by saturated aqueous K2CO3. The organic layer was separated, and the aqueous phase extracted with Et2O. The combined organics were then washed with water, saturated NaCl, dried over Na2SO4, filtered and evaporated to give the title compound (580 mg, 31%).

1. additionafter complete addition the mixture
2. customThe reaction was quenched by the careful addition of water (2 ml)
3. customThe organic layer was separated
4. extractionthe aqueous phase extracted with Et2O
5. washThe combined organics were then washed with water, saturated NaCl
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated

ORD record

ord-70c0a564fe19457bb2f78c2a0536a2d3

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07285563B2