Sodium Carbonate → HCID 10271246, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxy-2-(6-methoxy-2,4-dimethylphenyl)-6-methylpyrimidin-5-ylmethylsulfonate (203 mg, 0.5 mmol), 2-methoxy-4-fluorophenylboronic acid (169 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (29 mg, 5 mol %) in toluene (5 mL) and sodium carbonate (1M in water, 2 mL) is heated at 95° C. (oil bath temperature) in a pressure tube for 14 hours. The reaction is cooled to room temperature, diluted with ethyl acetate, washed with NaOH (2M) and then brine (2×50 mL). The solvents are dried (sodium sulfate) and removed under reduced pressure. Flash chromatography of the crude product (50% ethyl acetate in hexanes) yields 4-fluoro-1-methoxy-2-[4-methoxy-2-(6-methoxy-2,4-dimethylphenyl)-6-methylpyrimidin-5-yl]benzene (Compound 7) as an oil. MS: 383. NMR (400 MHz, CDCl3): 2.14 (s, 3H), 2.28 (s, 3H), 2.35 (s, 3H), 3.76 (s, 3H), 3.77 (s, 3H), 3.88 (s, 3H), 6.66 (s, 1H), 6.70 (s, 1H), 6.91-6.98 (m, 2H), 7.04-7.09 (m, 1H).

Provenance & Evidence