3-Fluoroaniline → 4-[2-[(3-fluorophenyl)amino]-4-pyridinyl]-N-[1-methyl-2-(methylthio)ethyl]-2-pyrimidinamine

Temperature

110 °C

To a solution of 4-(2-chloro-4-pyridinyl)-N-[1-methyl-2-(methylthio)ethyl]-2-pyrimidinamine (i.e., the product of Step C) (150 mg, 0.5 mmol) in toluene (6.0 mL) was added 3-fluoroaniline (108 μL, 1.1 mmol), palladium(II) acetate (24 mg, 0.12 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene ((±)-BINAP) (40 mg, 0.06 mmol) and cesium carbonate (700 mg, 2.2 mmol); the resulting mixture was stirred at 110° C. for 13 h. The mixture was allowed to cool and silica gel (300 mg) was added. The excess solvent was removed under reduced pressure, and the resulting solid was chromatographed on silica gel eluted with 5% to 60% ethyl acetate in hexanes to give 60 mg of the title compound as a yellow solid, m.p. 104-107° C.

1. temperatureto cool
2. additionsilica gel (300 mg) was added
3. customThe excess solvent was removed under reduced pressure
4. customthe resulting solid was chromatographed on silica gel
5. washeluted with 5% to 60% ethyl acetate in hexanes

ORD record

ord-1c165ee1b2534e5dbcda429e26298761

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026359B2