Cesium carbonate → HCID 66600008, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (506 mg, 2.004 mmol), 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (480 mg, 2.004 mmol, Combi-Blocks, Inc., San Diego, Calif.), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (164 mg, 0.200 mmol), and cesium carbonate (0.321 mL, 4.01 mmol) in dioxane (4 mL) and water (0.5 mL) was stirred at 100° C. for 30 min. The mixture was cooled down to room temperature. The reaction mixture was diluted with water (5 mL) and extracted with EtOAc (2×30 mL), The organic extract was washed with saturated NaCl (2 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give a yellow solid. The crude material was adsorbed onto a plug of silica gel and purified by flash chromatography eluting with 10% MeOH in CH2Cl2 to provide 6-(4-chloropyridin-3-yl)-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (98 mg, 15% yield) as light-yellow glass. 1H NMR (300 MHz, CDCl3) δ 8.83 (s, 1H); 8.61 (d, J=5.41 Hz, 1H); 8.27 (s, 1H); 7.50 (d, J=5.41 Hz, 1H); 5.87 (d, J=10.08 Hz, 1H); 4.20 (d, J=11.25 Hz, 1H); 3.84 (t, J=11.33 Hz, 1H); 3.48 (d, J=5.41 Hz, 1H); 2.90 (s, 3H); 1.99-2.29 (m, 3H); 1.64-1.95 (m, 3H). m/z (ESI, +ve ion) 330 (M+H)+.

Provenance & Evidence