Acetic Acid → Methyl 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzoate

To a stirring solution of methyl 3-(6-chloropyrimidin-4-ylamino)benzoate (1.0 g, 3.8 mmol) and 4-phenoxy aniline (0.703 g, 3.8 mmol) in ethanol (5 mL) was added acetic acid (0.22 mL) and the reaction mixture was heated at 100° C. for 48 h. The reaction mixture was cooled, ethanol was removed under reduced pressure and the residue was dissolved in ethyl acetate (50 mL). It was washed with NaHCO3 solution (5 mL) and brine (5 mL), was dried over Na2SO4 and was concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1) to yield methyl 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzoate (1 g, 66%) as an off-white solid.

1. temperatureThe reaction mixture was cooled
2. customethanol was removed under reduced pressure
3. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
4. washIt was washed with NaHCO3 solution (5 mL) and brine (5 mL)
5. dry with materialwas dried over Na2SO4
6. concentrationwas concentrated under reduced pressure
7. customThe residue was purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1)

ORD-Eintrag

ord-00e682a3aef942919f39b76b060bd933

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08748606B2