Chlorotrimethylsilane → 2-{[4-(Trimethylsilyl)but-3-yn-1-yl]oxy}pyrimidine

To a solution of diisopropylamine (1.37 g, 13.5 mmol) in tetrahydrofuran (20 mL) was added 1.6M butyllithium/hexane solution (8.44 mL, 13.5 mmol) at −78° C., and the mixture was stirred for 2 hr. A solution of 2-(but-3-yn-1-yloxy)pyrimidine (1.00 g, 6.75 mmol) in tetrahydrofuran (2.5 mL) was added thereto, and the mixture was stirred for 1 hr. Chlorotrimethylsilane (1.80 mL, 14.2 mmol) was added, the reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (1.43 g, yield 91%).

1. stirringthe mixture was stirred for 1 hr
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

ORD record

ord-2da8951cb0b4462e81d5780cf4b0fb8d

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273761B2