A solution of 9-BBN (9-borabicyclo[3.3.1]nonane) in THF (0.5 M, 6.0 mL, 3.0 mmol) is added to a solution of 2-methyl-1-butene (210 mg, 3.0 mmol) in THF. The mixture is heated at reflux, under a nitrogen atmosphere for 12 hours and cooled. 1-(5-Bromo-3,6-diethylpyrazin-2-yl)-2,4-dimethoxybenzene (664 mg, 2.0 mmol), tetrakis(triphenylphosphine) palladium(0) (50 mg), and sodium hydroxide (3.0 M, 3.0 mL, 3.0 mmol) are added to the solution. The mixture is heated at 50 C for 12 hours and cooled. 30% Hydrogen peroxide (1 mL) is added, the solution stirred for 1 hour and the reaction mixture extracted with ether. The combined extracts are dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography, eluting with 40% ether in hexanes to give 1-[3,6-diethyl-5-(2-methylbutyl)pyrazin-2-yl]-2,4-dimethoxybenzene (393 mg).
