triethylamine; 1,1'-carbonyldiimidazole in dichloromethane

1: 1,1'-carbonyldiimidazole; 6-(4-aminophenyl)-5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione With triethylamine in dichloromethane T=20°C; 42 h; 2: N-methoxyamine hydrochloride in dichloromethane T=0 - 20°C; 3 h;

pyridine; triethylamine in N,N-dimethyl acetamide; water

triethylamine in dichloromethane T=0 - 20°C; 3 h; Cooling with ice;

1.1: NH4OAc; AcOH / toluene / 20 h / Heating 1.2: 67 percent / sulfur / ethanol / 2 h / 65 °C 2.1: pyridine / 2 h / 45 °C 3.1: 50.4 g / NaOMe / methanol / 6 h / 20 °C 4.1: 90 percent / KI; K2CO3 / dimethylformamide / 4 h / 20 °C 5.1: NBS; AIBN / chlorobenzene / 1.5 h / 90 °C 6.1: 33.0 g / i-Pr2NEt / dimethylformamide / 2 h / 20 °C 7.1: 87 percent / HCl; HCO2H / 10 percent Pd/C/water / diethyl ether / 3.5 h / 20 °C / atmospheric pressure 8.1: Et3N / CH2Cl2 / 24 h / 20 °C 8.2: 71 percent / Et3N / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: 90 percent / KI; K2CO3 / dimethylformamide / 4 h / 20 °C 2.1: NBS; AIBN / chlorobenzene / 1.5 h / 90 °C 3.1: 33.0 g / i-Pr2NEt / dimethylformamide / 2 h / 20 °C 4.1: 87 percent / HCl; HCO2H / 10 percent Pd/C/water / diethyl ether / 3.5 h / 20 °C / atmospheric pressure 5.1: Et3N / CH2Cl2 / 24 h / 20 °C 5.2: 71 percent / Et3N / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: pyridine / 2 h / 45 °C 2.1: 50.4 g / NaOMe / methanol / 6 h / 20 °C 3.1: 90 percent / KI; K2CO3 / dimethylformamide / 4 h / 20 °C 4.1: NBS; AIBN / chlorobenzene / 1.5 h / 90 °C 5.1: 33.0 g / i-Pr2NEt / dimethylformamide / 2 h / 20 °C 6.1: 87 percent / HCl; HCO2H / 10 percent Pd/C/water / diethyl ether / 3.5 h / 20 °C / atmospheric pressure 7.1: Et3N / CH2Cl2 / 24 h / 20 °C 7.2: 71 percent / Et3N / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: pyridine / 2 h / 45 °C 2.1: 50.4 g / NaOMe / methanol / 6 h / 20 °C 3.1: 90 percent / KI; K2CO3 / dimethylformamide / 4 h / 20 °C 4.1: NBS; AIBN / chlorobenzene / 1.5 h / 90 °C 5.1: 33.0 g / i-Pr2NEt / dimethylformamide / 2 h / 20 °C 6.1: 87 percent / HCl; HCO2H / 10 percent Pd/C/water / diethyl ether / 3.5 h / 20 °C / atmospheric pressure 7.1: Et3N / CH2Cl2 / 24 h / 20 °C 7.2: 71 percent / Et3N / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: 90 percent / KI; K2CO3 / dimethylformamide / 4 h / 20 °C 2.1: NBS; AIBN / chlorobenzene / 1.5 h / 90 °C 3.1: 33.0 g / i-Pr2NEt / dimethylformamide / 2 h / 20 °C 4.1: 87 percent / HCl; HCO2H / 10 percent Pd/C/water / diethyl ether / 3.5 h / 20 °C / atmospheric pressure 5.1: Et3N / CH2Cl2 / 24 h / 20 °C 5.2: 71 percent / Et3N / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: 50.4 g / NaOMe / methanol / 6 h / 20 °C 2.1: 90 percent / KI; K2CO3 / dimethylformamide / 4 h / 20 °C 3.1: NBS; AIBN / chlorobenzene / 1.5 h / 90 °C 4.1: 33.0 g / i-Pr2NEt / dimethylformamide / 2 h / 20 °C 5.1: 87 percent / HCl; HCO2H / 10 percent Pd/C/water / diethyl ether / 3.5 h / 20 °C / atmospheric pressure 6.1: Et3N / CH2Cl2 / 24 h / 20 °C 6.2: 71 percent / Et3N / CH2Cl2 / 3 h / 20 °C View Scheme