palladium diacetate; tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine in isopropyl alcohol; toluene T=105°C; 24 h;

1: pyrimidine-2-carboxamidine hydrochloride With potassium hydroxide in dichloromethane; water 2: 1,2,3-triazine in acetonitrile T=60°C; Diels-Alder reaction; 5 h; regioselective reaction;

copper in N,N-dimethyl-formamide T=80 - 130°C; Ullmann coupling; 7 h;

nickel diacetate; triphenylphosphine; sodium t-butanolate in ethylene glycol dimethyl ether T=25°C; 0.00472222 h;

in acetonitrile T=60°C; Diels-Alder reaction; 5 h; regioselective reaction;

in tetrahydrofuran byproducts: NaCl; Ar atmosphere, addn. of solid ligand to soln. of metal complex at 20°C, stirring (20°C, 30 min); removement of solvent (vacuum), dissolution (THF), chromy. (silica gel, elution of byproducts with Et2O, elution of main product with THF), evapn. of solvent; elem. anal.;

in tetrahydrofuran byproducts: NaCl; Ar atmosphere, addn. of solid ligand to soln. of metal complex at 20°C, stirring (20°C, 30 min); removement of solvent (vacuum), dissolution (THF), chromy. (silica gel, elution of byproducts with Et2O, elution of main product with THF), evapn. of solvent; elem. anal.;

1: 85 percent / Br2 / 150 °C 2: 62 percent / CuI; iPr2NH / PdCl2(PPh3)2 / tetrahydrofuran 3: 100 percent / KF / methanol / 20 °C View Scheme

bromine T=150°C;