1: 1.)2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT), N-methylmorpholine (NMM), 2.) N-methylmorpholine (NMM) / 1.) CH2Cl2, 0 deg C, 3 h, 2.) CH2Cl2, RT, 12 h 2: H2 / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr 3: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO3 / CH2Cl2 / 16 h / Ambient temperature 4: trifluoroacetic acid (TFA) / CH2Cl2 / 2 h / Ambient temperature View Scheme

triethylsilane; trifluoroacetic acid in dichloromethane 0.583333 h; Ambient temperature;

sodium hydroxide in tetrahydrofuran T=25°C;

1: conc. H2SO4 / CH2Cl2 2: 89.7 percent / 0.25 N NaOH / tetrahydrofuran / 25 °C View Scheme

sodium hydroxide in methanol T=20°C;

sodium hydroxide in 1,4-dioxane

1: H2SO4 / CH2Cl2 / 72 h / 20 °C 2: aq. NaOH / methanol / 20 °C View Scheme

1: 91 percent / aq. Na2CO3 / CH2Cl2; toluene / 20 °C 2: H2SO4 / CH2Cl2 / 72 h / 20 °C 3: aq. NaOH / methanol / 20 °C View Scheme

1: 99 percent / SOCl2 / 3.5 h 2: 91 percent / aq. Na2CO3 / CH2Cl2; toluene / 20 °C 3: H2SO4 / CH2Cl2 / 72 h / 20 °C 4: aq. NaOH / methanol / 20 °C View Scheme

1: 91 percent / aq. Na2CO3 / CH2Cl2; toluene / 20 °C 2: H2SO4 / CH2Cl2 / 72 h / 20 °C 3: aq. NaOH / methanol / 20 °C View Scheme