1.1: aq. NaOH / 2 h / 20 °C 1.2: aq. H2SO4 / 3 h / 0 °C 1.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 2.1: 4-methylmorpholine; 2-chloro-4,6-dimethoxy-1,3,5-triazine / dimethylformamide / 2 h / 20 °C 2.2: 62 percent / 4-methylmorpholine / dimethylformamide / 3.5 h / 20 °C View Scheme

1: 98 percent / Pd(OAc)2 2: 72 percent / NaOH / ethanol 3: 90 percent / CH3SO2Cl; Et3N 4: 91 percent / ethyl acetate; H2O / 24 h / 50 °C 5: 57 percent 6: 62 percent / 4-methylmorpholine; 2-chloro-4,6-dimethoxy-1,3,5-triazine / 20 °C View Scheme

1: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 2: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 3: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 4: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 5: CF3COOH, H2O 6: diethyl phosphorocyanidate, triethylamine / dimethylformamide View Scheme

1: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 2: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 3: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 4: CF3COOH, H2O 5: diethyl phosphorocyanidate, triethylamine / dimethylformamide View Scheme

1: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 2: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 3: CF3COOH, H2O 4: diethyl phosphorocyanidate, triethylamine / dimethylformamide View Scheme

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

1: CF3COOH, H2O 2: diethyl phosphorocyanidate, triethylamine / dimethylformamide View Scheme

1: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 2: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 3: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale 4: 2-chloro-4,6-dimethoxy-[1,3,5]triazine; 4-methylmorpholine N-oxide / N,N-dimethyl-formamide / 1.5 h / 25 °C / |Large scale View Scheme

1: palladium dichloride; triphenylphosphine; copper(l) iodide; diethylamine / ethyl acetate / 4 h / 50 °C / |Large scale 2: hydrogen; 5 palladium on charcoal / dichloromethane / 3.5 h / 3345.86 Torr / |Inert atmosphere; |Autoclave; |Large scale 3: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / |Large scale 4: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 5: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 6: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale 7: 2-chloro-4,6-dimethoxy-[1,3,5]triazine; 4-methylmorpholine N-oxide / N,N-dimethyl-formamide / 1.5 h / 25 °C / |Large scale View Scheme

diethyl cyanophosphonate; triethylamine in N,N-dimethyl-formamide Yield given;