1: 63 percent / triethylamine (TEA) / CH2Cl2 / 16 h / Ambient temperature 2: 76 percent / tetra-n-butylammonium hydrogen sulfate, aq. NaOH / CH2Cl2; H2O / 16 h 3: 94 percent / H2 / 10percent Pd/C / ethanol / 3 h / 760 Torr 4: 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 5: H2 / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr 6: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO3 / CH2Cl2 / 16 h / Ambient temperature 7: trifluoroacetic acid (TFA) / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 76 percent / tetra-n-butylammonium hydrogen sulfate, aq. NaOH / CH2Cl2; H2O / 16 h 2: 94 percent / H2 / 10percent Pd/C / ethanol / 3 h / 760 Torr 3: 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 4: H2 / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr 5: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO3 / CH2Cl2 / 16 h / Ambient temperature 6: trifluoroacetic acid (TFA) / CH2Cl2 / 2 h / Ambient temperature View Scheme

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

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

1: 94 percent / H2 / 10percent Pd/C / ethanol / 3 h / 760 Torr 2: 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 3: H2 / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr 4: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO3 / CH2Cl2 / 16 h / Ambient temperature 5: trifluoroacetic acid (TFA) / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: H2 / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr 2: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO3 / CH2Cl2 / 16 h / Ambient temperature 3: trifluoroacetic acid (TFA) / CH2Cl2 / 2 h / Ambient temperature View Scheme

trifluoroacetic acid in dichloromethane 2 h; Ambient temperature;

hydrogen; acetic anhydride; acetic acid; palladium on activated charcoal

1.1: NaH / tetrahydrofuran / 1 h / 20 °C 1.2: 30 percent / tetrahydrofuran / 3 h / Heating 2.1: NH2OH*HCl; MeONa / methanol / 48 h / 20 °C 3.1: HCO2H / 10 h / 20 °C 4.1: 43 percent / H2; Ac2O; AcOH / 10 percent Pd/C View Scheme

1: NH2OH*HCl; MeONa / methanol / 48 h / 20 °C 2: HCO2H / 10 h / 20 °C 3: 43 percent / H2; Ac2O; AcOH / 10 percent Pd/C View Scheme