ammonia; lithium 2 h;

1: 90 percent / liquid NH3, Li / 2 h 2: 85 percent / PBr3, pyridine / diethyl ether / 12 h / Ambient temperature 3: 1.) LiNH2, liquid NH3 / 1.) THF, 2 h, 2.) 20 min 4: 90 percent / Na, liquid NH3 / tetrahydrofuran / 1 h 5: 90 percent / pyridine / 12 h / Ambient temperature View Scheme

1: 90 percent / liquid NH3, Li / 2 h 2: 85 percent / PBr3, pyridine / diethyl ether / 12 h / Ambient temperature 3: 1.) LiNH2, liquid NH3 / 1.) THF, 2 h, 2.) 20 min 4: 90 percent / Na, liquid NH3 / tetrahydrofuran / 1 h View Scheme

Multi-step reaction with 3 steps 1: 90 percent / liquid NH3, Li / 2 h2: 85 percent / PBr3, pyridine / diethyl ether / 12 h / Ambient temperature3: 1.) LiNH2, liquid NH3 / 1.) THF, 2 h, 2.) 20 min