6-(3-Methoxyphenyl)pyrimidin-4-amine synthesis

Yield:1192814-08-6 70%

Reaction Conditions:

with sodium carbonate;bis-triphenylphosphine-palladium(II) chloride in 1,2-dimethoxyethane;ethanol;water at 125; for 0.333333 h;Microwave irradiation;

Steps:

238.A

Step A: 6-(3-Methoxyphenyl)pyrimidin-4-amine A mixture of 6-chloropyrimidin-4-amine (0.324 g, 2.5 mmol), 3-methoxyphenylboronic acid (0.475 g, 3.13 mmol), Na₂CO₃ (0.795 g, 7.50 mmol) and bis(triphenylphosphine)palladium(II)chloride (0.035 g, 0.050 mmol) was suspended in DME/EtOH/water (15:2:3 mL), heated in the microwave synthesizer at 125° C. for 20 min and concentrated. The residue was purified by silica gel chromatography (10-60% ethyl acetate-hexanes) to afford 6-(3-methoxyphenyl)pyrimidin-4-amine (0.35 g, 1.74 mmol, 70% yield) as an off-white solid. LCMS R.T.=1.28; [M+H]⁺=201.98.

References:

US2009/270405,2009,A1 Location in patent:Page/Page column 134