sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride in ethanol; water; toluene T=120°C; 1 h; Inert atmosphereMicrowave irradiation;

sodium carbonate; PdCl2(PPh3)2 in ethanol; water; ethyl acetate; toluene

1: 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane; 4-bromo-1H-indazole With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate in dimethyl sulfoxide T=80°C; 40 h; Inert atmosphere; 2: 4-(2-chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]-pyrimidin-4-yl)morpholine With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate in ethanol; toluene T=130°C; Suzuki coupling; 1.5 h; Microwave irradiation;

1: With titanium(IV) isopropylate; triethylamine in chloroform Reflux; 2: With sodium cyanoborohydride in 1,2-dichloro-ethane T=20°C; 12 h;

1: With acetic acid; trimethyl orthoformate in dichloromethane 2 - 6 h; 2: With sodium tris(acetoxy)borohydride in dichloromethane 12 - 16 h; 3: With water; sodium hydrogencarbonate in dichloromethane

1: With sodium acetate; trimethyl orthoformate in acetonitrile T=45°C; 5 h; Inert atmosphereLarge scale; 2: With sodium tris(acetoxy)borohydride in acetonitrile 7 h; Inert atmosphereLarge scale; Solvent;

1: 2-chloro-4-(morpholin-4-yl)-thieno[3,2-d]pyrimidine With isopropylmagnesium chloride in tetrahydrofuran T=0°C; 0.5 h; Inert atmosphere; 2: With n-butyllithium in tetrahydrofuran; hexane T=-10°C; Inert atmosphere; 3: 1-((4-(methylsulfonyl)piperazin-1-yl)methyl)-1H-benzotriazole With zinc(II) chloride in tetrahydrofuran; hexane T=-20 - 10°C; 0.5 h; Inert atmosphere;

sodium tris(acetoxy)borohydride in 1,2-dichloro-ethane

N-ethyl-N,N-diisopropylamine in 3-methyl-1-butanol 11 h; Reflux;

1.1: trichlorophosphate / 10 h / Reflux 2.1: methanol / 1 h / 20 °C 3.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 11 h / -78 - 20 °C 4.1: titanium(IV) isopropylate; triethylamine / chloroform / Reflux 4.2: 12 h / 20 °C View Scheme