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

HRID 522880Notes

Reaction equation

HRID 522880 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]=1

Participants

4

Reactant 1

HCID 673767813-(4-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 625857233-(4-chlorophenyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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.

Workup

  1. filtrationThe reaction mixture was filtered through and
  2. concentrationconcentrated
  3. customPurification by flash chromatography (silica gel, 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-6db126ed972945b49dedaf0f059a6525
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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