Cesium carbonate → (R)-tert-butyl 3-((5-(2-(1H-pyrrol-1-yl)thiazol-4-yl)-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate

온도

100 °C

In a 40 mL vial chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl)]-palladium(II) (0.023 g, 0.029 mmol), tert-butyl 3-((5-iodo-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate (Compound (21) (0.15 g, 0.289 mmol), 2-(1H-pyrrol-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (0.088 g, 0.318 mmol) and CuCl (0.031 g, 0.318 mmol) were combined. This mixture was then evacuated and backfilled with argon. Then DMF (2.89 ml) and Cs2CO3 (0.376 g, 1.16 mmol) were added to this flask all under argon. This mixture was then heated at 100° C. for 18 h. The mixture was cooled, filtered, diluted with ethyl acetate (mL), washed with water, then dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified via column chromatography. (0-50% EtOAc/hexane) to give the title compound as a white solid. MS (m/z)=542 (M+H).

1. customThis mixture was then evacuated
2. temperatureThe mixture was cooled
3. filtrationfiltered
4. additiondiluted with ethyl acetate (mL)
5. washwashed with water
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified via column chromatography

ORD 기록

ord-edfc0df8dce94c6fa712bd82958981d8

출처 데이터셋

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09221809B2