Cesium carbonate → 6-(4-Chloropyridin-3-yl)-2-methylpyrimidin-4-amine

Temperatur

100 °C

A mixture of 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (239 mg, 998 μmol, Combi-Blocks, Inc., San Diego, Calif.), 6-chloro-2-methylpyrimidin-4-amine (143 mg, 998 μmol), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (81 mg, 100 μmol), cesium carbonate (160 μl, 1996 μmol) in dioxane (2 mL) and water (0.5 mL) was stirred at 100° C. for 10 min. The mixture was cooled down to room temperature. The reaction mixture was diluted with saturated NH4Cl (5 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL), dried over Na2SO4, filtered, concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with THF to give 6-(4-chloropyridin-3-yl)-2-methylpyrimidin-4-amine (32 mg, 15% yield). 1H NMR (300 MHz, MeOH) δ 8.66 (s, 1H); 8.57 (d, J=5.41 Hz, 1H); 7.66 (d, J=5.26 Hz, 1H); 6.64 (s, 1H); 2.04 (s, 3H). m/z (ESI, +ve ion) 221 (M+H)+.

1. temperatureThe mixture was cooled down to room temperature
2. extractionextracted with EtOAc (2×30 mL)
3. extractionThe organic extract
4. washwas washed with saturated NaCl (5 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customthe residue was purified by silica gel chromatography
9. washeluting with THF

ORD-Eintrag

ord-e36f47c679574d82bb1d3a8276c7e678

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08772480B2