1: 1) dibromodimethylhydantoin, 2) potassium carbonate / 1) acetone, water, 0 deg C, 2) methanol, room temperature, overnight 2: 84 percent / sodium azide, ammonium chloride / aq. ethanol / 72 h / 100 °C 3: 21 percent / diethylaminosulphur trifluoride / CH2Cl2 / 0.17 h / 0 °C 4: 99 percent / H2 / Lindlar / ethanol / 3 h / 760 Torr / Ambient temperature 5: 82 percent / dimethylformamide / Ambient temperature; overnight 6: 89 percent / p-toluenesulphonic acid / CH2Cl2; methanol / 3 h / Ambient temperature 7: 88 percent / aq. hydrochloric acid / 0.5 h / Heating View Scheme

1: 1.) dimethyldibromohydantoin, 2.) K2CO3 / 1.) H2O, acetone, 0 deg C, 2.) MeOH 2: 84 percent / NaN3, NH4Cl / ethanol; H2O / 90 °C 3: diethylaminosulphur trifluoride (DAST) / CH2Cl2 / 0 °C 4: H2 / Lindlar catalyst / ethanol 5: benzene; dimethylformamide / 18 h / -15 - 20 °C 6: toluene-p-sulphonic acid / methanol; CH2Cl2 7: HCl / 0.5 h / Heating View Scheme

1: 1) dibromodimethylhydantoin, 2) potassium carbonate / 1) acetone, water, 0 deg C, 2) methanol, room temperature, overnight 2: 84 percent / sodium azide, ammonium chloride / aq. ethanol / 72 h / 100 °C 3: 21 percent / diethylaminosulphur trifluoride / CH2Cl2 / 0.17 h / 0 °C 4: 99 percent / H2 / Lindlar / ethanol / 3 h / 760 Torr / Ambient temperature 5: 82 percent / dimethylformamide / Ambient temperature; overnight 6: 89 percent / p-toluenesulphonic acid / CH2Cl2; methanol / 3 h / Ambient temperature 7: 88 percent / aq. hydrochloric acid / 0.5 h / Heating View Scheme

1: 1.) dimethyldibromohydantoin, 2.) K2CO3 / 1.) H2O, acetone, 0 deg C, 2.) MeOH 2: 84 percent / NaN3, NH4Cl / ethanol; H2O / 90 °C 3: diethylaminosulphur trifluoride (DAST) / CH2Cl2 / 0 °C 4: H2 / Lindlar catalyst / ethanol 5: benzene; dimethylformamide / 18 h / -15 - 20 °C 6: toluene-p-sulphonic acid / methanol; CH2Cl2 7: HCl / 0.5 h / Heating View Scheme

1: 1.) dimethyldibromohydantoin, 2.) K2CO3 / 1.) H2O, acetone, 0 deg C, 2.) MeOH 2: 84 percent / NaN3, NH4Cl / ethanol; H2O / 90 °C 3: diethylaminosulphur trifluoride (DAST) / CH2Cl2 / 0 °C 4: H2 / Lindlar catalyst / ethanol 5: Et3N / CH2Cl2 / Ambient temperature 6: H2 / Raney Ni / dioxane 7: H+ 8: NH3(l) / 18 h / Ambient temperature 9: aq. HCl / 0.08 h View Scheme

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane 0 deg C to room temperature, overnight;

1: 68 percent / lithium aluminum hydride / diethyl ether / 0.5 h / 0 °C 2: 98 percent / triethylamine, DMAP / CH2Cl2 / 0 deg C to room temperature, overnight View Scheme

1: 69 percent / hydrogen chloride / -35 °C 2: 1) magnesium / 1) THF, -12 to -7 deg C, 1 h, 2) to room temperature, overnight 3: 68 percent / lithium aluminum hydride / diethyl ether / 0.5 h / 0 °C 4: 98 percent / triethylamine, DMAP / CH2Cl2 / 0 deg C to room temperature, overnight View Scheme

1: 1) magnesium / 1) THF, -12 to -7 deg C, 1 h, 2) to room temperature, overnight 2: 68 percent / lithium aluminum hydride / diethyl ether / 0.5 h / 0 °C 3: 98 percent / triethylamine, DMAP / CH2Cl2 / 0 deg C to room temperature, overnight View Scheme