3-(4-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyrazine → 3-(4-chlorophenyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][N:15]=[CH:16][C:11]3=[N:10][N:9]=2)=[CH:4][CH:3]=1>[Pd].C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH2:13][CH2:14][NH:15][CH2:16][C:11]3=[N:10][N:9]=2)=[CH:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
3-(4-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyrazine (2.01 g) was hydrogenated under atmospheric hydrogen with 10% Pd/C (400 mg Celite® (diatomaceous earth)) as a catalyst in ethanol (20 mL) at RT for 18 h. The reaction mixture was filtered through and concentrated. Purification by flash chromatography (silica gel, 10% methanol/dichloromethane) afforded 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (86% yield) as a viscous oil.