Borane;tetrahydrofuran → HCID 58169431, compound

Participants

Reaction Steps

A solution of compound 1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen-2-yl)ethanone (50 mg, 0.15 mmol, 1.0 eq) in dry THF (5 mL) was added dropwise to the mixture of (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2] oxazaborole (0.22 mL, 0.22 mmol, 1.5 eq) and BH3.THF (0.44 mL, 0.44 mmol, 3.0 eq) in dry THF (2 mL) at 0° C. The mixture was stirred for 3 h, quenched with isopropylalcohol and concentrated. The residue was purified by silica gel column chromatography, then, recrystallized with THF/CH2Cl2/Petroleum ether to afford (R)-1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen-2-yl)ethanol (Compound 147) (21 mg, 42%).

Provenance & Evidence