Potassium Carbonate → 2-(4-(5-Bromo-2-methyl-2,3-dihydrobenzofuran-2-yl)piperidin-1-yl)-5-cyclopropylpyrimidine

A mixture of 4-(5-bromo-2-methyl-2,3-dihydrobenzofuran-2-yl)piperidine (0.3 g, 1.013 mmol), 2-chloro-5-cyclopropylpyrimidine (0.204 g, 1.317 mmol) and K2CO3 (0.42 g, 3.04 mmol) in DMF (5 mL) was heated in 90° C. oil bath overnight. At the conclusion of this period, the reaction mixture was cooled to room temperature, quenched with H2O (5 mL), and then extracted with EtOAc (3×5 mL). The combined organic layers were washed with H2O (3×5 mL) and brine (5 mL). The organic layer was separated, dried (Na2SO4), filtered, and concentrated to yield a residue. The residue was purified by column chromatography (silica gel, hexanes/EtOAc gradient 0 to 35% EtOAc) to afford Compound 11E as white solid (0.315 g, 31% yield). LC/MS (m/z)=414 (M+H)+.

1. temperatureAt the conclusion of this period, the reaction mixture was cooled to room temperature
2. customquenched with H2O (5 mL)
3. extractionextracted with EtOAc (3×5 mL)
4. washThe combined organic layers were washed with H2O (3×5 mL) and brine (5 mL)
5. customThe organic layer was separated
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customto yield a residue
10. customThe residue was purified by column chromatography (silica gel, hexanes/EtOAc gradient 0 to 35% EtOAc)

ORDレコード

ord-20c0920ef20d422784b892a7d5a6b35c

出典データセット

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08729084B2