in xylene 2 h; Reflux;

tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane T=110 - 120°C; 10 h;

in tetrahydrofuran; toluene T=0°C; 5 h; Inert atmosphere;

in acetonitrile T=22°C; Diels-Alder reaction; 0.166667 h; regiospecific reaction;

sodium methylate in methanol T=180°C; 7 h;

1: 2-methyl-5-bromo-1,3-pyrimidine With iron sulphate heptahydrate; sulfuric acid in water; toluene T=-10°C; Minisci reaction; 2: α-hydroxy-α-(ethoxycarbonyl)ethyl hydroperoxide With acetic acid in water; toluene T=-10 - 0°C; Minisci reaction; 1.5 h; 3: With sodium hydroxide in water; toluene pH=7; Cooling with ice; regioselective reaction;

n-butyllithium 1.) THF, -98 deg C, 5 min, 2.) THF, from -78 deg C to RT; Yield given. Multistep reaction;

1: bis(triphenylphosphine)palladium(II) chloride / diethyl ether; N,N-dimethyl-formamide 2: sodium hydrogencarbonate; hydrogenchloride / hexadeuterioacetone View Scheme