4-methyl-morpholine; 2-chloro-4,6-dimethoxy-[1,3,5]triazine; sodium hydroxide in ethanol; water T=40°C; 3 h;

sulfuric acid; trifluoroacetic acid T=20°C; deprotection;

4-methyl-morpholine in N,N-dimethyl-formamide

1: 65 percent / Et3N; CuI; (o-tolyl)3P / Pd(OAc)2 / dimethylformamide 2: 29.5 percent / conc. H2SO4; anisole / trifluoroacetic acid / 4 h / 20 °C View Scheme

1.1: 86 percent / Mn(OAc)3*2H2O; Cu(OAc)2*H2O / acetic acid / 20 °C 2.1: 85 percent / P4S10 / tetrahydrofuran / Heating 3.1: NaOMe / methanol / 0.5 h / 20 °C 3.2: 68 percent / methanol / 1 h / 90 °C / 15 Torr 4.1: 65 percent / Et3N; CuI; (o-tolyl)3P / Pd(OAc)2 / dimethylformamide 5.1: 29.5 percent / conc. H2SO4; anisole / trifluoroacetic acid / 4 h / 20 °C View Scheme

1: 94 percent / toluene / 1 h / Heating 2: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / 4 h 3: 99 percent / LiBH4 / diethyl ether / 15 h / Ambient temperature 4: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 5: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 6: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 7: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 8: CF3COOH, H2O 9: diethyl phosphorocyanidate, triethylamine / dimethylformamide View Scheme

1: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / 4 h 2: 99 percent / LiBH4 / diethyl ether / 15 h / Ambient temperature 3: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 4: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 5: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 6: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 7: CF3COOH, H2O 8: diethyl phosphorocyanidate, triethylamine / dimethylformamide View Scheme

1: manganic triacetate dihydrate; cupric acetate hydrate 2: P2S5 / tetrahydrofuran 4: Pd(OAc)2 5: 30 percent / H2SO4; TFA / 20 °C View Scheme

1.1: 68 percent / aq. NaOH / ethanol / 48 h / 38 °C 2.1: 90 percent / CH3SO2Cl; Et3N / CH2Cl2 / 0 - 20 °C 3.1: 91 percent / H2O; ethyl acetate / 24 h / 50 °C 4.1: aq. NaOH / 2 h / 20 °C 4.2: aq. H2SO4 / 3 h / 0 °C 4.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 5.1: 4-methylmorpholine; 2-chloro-4,6-dimethoxy-1,3,5-triazine / dimethylformamide / 2 h / 20 °C 5.2: 62 percent / 4-methylmorpholine / dimethylformamide / 3.5 h / 20 °C View Scheme

1.1: 90 percent / CH3SO2Cl; Et3N / CH2Cl2 / 0 - 20 °C 2.1: 91 percent / H2O; ethyl acetate / 24 h / 50 °C 3.1: aq. NaOH / 2 h / 20 °C 3.2: aq. H2SO4 / 3 h / 0 °C 3.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 4.1: 4-methylmorpholine; 2-chloro-4,6-dimethoxy-1,3,5-triazine / dimethylformamide / 2 h / 20 °C 4.2: 62 percent / 4-methylmorpholine / dimethylformamide / 3.5 h / 20 °C View Scheme