tetramethyl-ammonium fluoride; acetic acid in N,N-dimethyl-formamide T=20°C;

methanol; sodium methylate T=30 - 40°C;

1: 35 percent / TMSOTf / acetonitrile / 0.33 h / Heating 2: NH3 / 1,2-dimethoxy-ethane / 72 h / 20 °C 3: 0.44 g / NH3 / methanol / 48 h / 20 °C View Scheme

ammonia in ethanol 72 h; Ambient temperature; Title compound not separated from byproducts;

1: sodium iodide / acetonitrile; 1,1-dimethylpropan-1-ol / 24 h / 20 °C / |Inert atmosphere 2: sodium methylate / methanol / 7 h / 33 °C / |Inert atmosphere View Scheme

1.1: N,O-bis(trimethylsilyl) trifluoroacetamide / acetonitrile / 1 h / Inert atmosphere; Reflux 1.2: 1 h / Reflux 2.1: pyridine; hydrazine hydrate; acetic acid / 75 - 80 °C / Inert atmosphere 3.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 4.1: H2NC(=NH)NH2*carbonate / dichloromethane; ethyl acetate / 60 °C 4.2: 80 °C 5.1: sodium methylate; methanol / 30 - 40 °C View Scheme

1.1: N,O-bis(trimethylsilyl) trifluoroacetamide / acetonitrile / 1 h / Inert atmosphere; Reflux 1.2: 1 h / Reflux 2.1: pyridine; hydrazine hydrate; acetic acid / 75 - 80 °C / Inert atmosphere 3.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 4.1: H2NC(=NH)NH2*carbonate / dichloromethane; ethyl acetate / 60 °C 4.2: 80 °C 5.1: sodium methylate; methanol / 30 - 40 °C View Scheme

1.1: pyridine; hydrazine hydrate; acetic acid / 75 - 80 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: H2NC(=NH)NH2*carbonate / dichloromethane; ethyl acetate / 60 °C 3.2: 80 °C 4.1: sodium methylate; methanol / 30 - 40 °C View Scheme

1.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: H2NC(=NH)NH2*carbonate / dichloromethane; ethyl acetate / 60 °C 2.2: 80 °C 3.1: sodium methylate; methanol / 30 - 40 °C View Scheme

lithium hydroxide; ammonia 1.) ethanol, RT, 3 d, 2.) acetonitrile, RT, 3 h; Yield given. Multistep reaction;