Potassium Phosphate, Tribasic → HCID 46927505, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one Part A of Procedure 11 (40 mg, 0.12 mmol), (E)-4-chlorostyrylboronic acid (56 mg, 0.30 mmol), potassium phosphate, tribasic (78 mg, 0.37 mmol), and palladiumtetrakis (7 mg, 6.16 μmol) in DMF (1 mL) was stirred under nitrogen at 55° C. for 1 hour. The mixture was diluted with DCM, washed with water, sat. NaHCO3 and brine, then dried (Na2SO4) and concentrated to afford the crude product. The crude product was purified using ISCO flash chromatography (silica gel/hexanes-ethyl acetate 100:0 to 0:100 gradient). The product was re-purified using HPLC (C18 column/10:90 to 90:10 MeOH—H2O) to afford the desired product (E)-6-(4-chlorostyryl)-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one J-1 (16.8 mg, 0.039 mmol, 31% yield) as a light yellow solid. LC/MS 427 (M+H)+, tR 0.97 min (method 5); 1H NMR (400 MHz, CHLOROFORM-d) δ 8.15 (1H, s), 7.76 (1H, d, J=15.56 Hz), 7.53 (2H, d, J=8.28 Hz), 7.38 (2H, d, J=8.28 Hz), 7.01 (1H, d, J=8.03 Hz), 6.82-6.98 (3H, m), 6.46 (1H, s), 3.89 (5H, br. s.), 1.37 (6H, s).

Provenance & Evidence