(Dimethyl sulfide)trihydroboron → HCID 118390087, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[5-[[5-chloro-2-[(1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl]amino]-hexahydrocyclopenta[c]pyrrol-2(1H)-yl]-2,2,2-trifluoro-ethanone (0.89 g, 2.10 mmol) in THF (20 mL) was added a solution of borane dimethyl sulfide complex (1 mmol/L in THF, 6 mL, 6 mmol) at 0° C. After addition, the reaction mixture was stirred at 0° C. for 10 min and then heated to reflux overnight. The reaction was quenched with 6 M HCl aqueous solution (2 mL) then stirred at rt for 1 h and concentrated in vacuo. The residue was adjusted to pH=10 with a 50% NaOH solution, then diluted with water (50 mL), and extracted with EtOAc (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/50) to give the title compound as a beige solid (0.16 g, 19%).

Provenance & Evidence