3-(4-Pyridinyl)[1,2,4]triazolo[4,3-a]pyrazine → 3-(Pyridin-4-yl)-5,6,7,8-tetrahydro-(1,2,4)triazolo(4,3-a)pyrazine

HRID 1889063

Reaction equation

HRID 1889063 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]3[CH:12]=[CH:13][N:14]=[CH:15][C:10]3=[N:9][N:8]=2)=[CH:3][CH:2]=1>[Pd].C(O)C>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:11]3[CH2:12][CH2:13][NH:14][CH2:15][C:10]3=[N:9][N:8]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 665992353-(4-Pyridinyl)[1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 625876923-(Pyridin-4-yl)-5,6,7,8-tetrahydro-(1,2,4)triazolo(4,3-a)pyrazineYield 52.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(4-Pyridinyl)[1,2,4]triazolo[4,3-a]pyrazine (538 mg, 2.73 mmol) was hydrogenated under atmospheric hydrogen with 10% Pd/C as a catalyst in ethanol at ambient temperature for 36 hours. The catalyst was filtered off and the solvent was evaporated. The residue was purified on silica gel chromatography using 0-20% of 2M methanol in ammonia—Dichloromethane as eluent to give 3-(4-pyridinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.288 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated
  3. customThe residue was purified on silica gel chromatography

Sources & evidence

ORD record
ord-07436cf1f0874c7995d3038562c02bd0
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Linked notes

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