Hexane → HCID 89734168, compound

Temperature

-78 °C

To a solution of 5-bromo-2-trifluoromethyl-pyrimidine (200 mg, 0.879 mmol) in dry diethyl ether (1.5 ml) at −78° C. was added a 2.5 M solution of n-butyllithium in hexane (0.32 ml, 0.811 mmol) and the mixture was stirred at −78° C. for 15 min. A solution of (S)-2-methyl-propane-2-sulfinic acid propylideneamide (Comp. No. 13b) (110 mg, 0.676 mmol) in dry toluene (1 ml) was added at −78° C., the mixture was stirred for 5 min at −78° C. and then poured into a saturated aqueous ammonium chloride solution. The mixture was extracted 3 times with dichloromethane, dried over sodium sulfate, and after evaporation of all solvents the crude product was purified by flash chromatography (silica gel, elution with heptane/ethyl acetate) to give 15 mg of (S)-2-methyl-propane-2-sulfinic acid ((R)-1-(2-trifluoromethyl-pyrimidin-5-yl)-propyl)amide (LC/MS (method 7): Rt=1.37 min; m/z=310.1 (M+H+)) and 20 mg of (S)-2-methyl-propane-2-sulfinic acid ((R)-1-(2-trifluoromethyl-pyrimidin-5-yl)-propyl)amide (LC/MS (method 7): Rt=1.37 min; m/z=310.1 (M+H+)).

1. stirringthe mixture was stirred for 5 min at −78° C.
2. extractionThe mixture was extracted 3 times with dichloromethane
3. dry with materialdried over sodium sulfate
4. customafter evaporation of all solvents the crude product
5. customwas purified by flash chromatography (silica gel, elution with heptane/ethyl acetate)

ORD record

ord-1ae6be8db59849b8a77c315c205d4a96

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09284333B2