(Dimethyl sulfide)trihydroboron → HCID 118390087, compound

Temperature

0 °C

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%).

1. additionAfter addition
2. temperatureheated
3. temperatureto reflux overnight
4. customThe reaction was quenched with 6 M HCl aqueous solution (2 mL)
5. stirringthen stirred at rt for 1 h
6. concentrationconcentrated in vacuo
7. additiondiluted with water (50 mL)
8. extractionextracted with EtOAc (100 mL×3)
9. washThe combined organic phases were washed with brine (100 mL)
10. dry with materialdried over anhydrous Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/50)

ORD record

ord-ba31f6c1df534567a1ba330f10d58e54

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403801B2