Ammonium formate → 3-Phenyl-2-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

HRID 406252Notes

Reaction equation

HRID 406252 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]3[N:13]=[CH:14][CH:15]=[CH:16][C:10]3=[N:9][C:8]=2[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>CO.[Pd]>[C:1]1([C:7]2[N:12]=[C:11]3[NH:13][CH2:14][CH2:15][CH2:16][C:10]3=[N:9][C:8]=2[C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 590904003-Phenyl-2-p-tolylpyrido[2,3-b]pyrazine

Product 1

HCID 666659633-Phenyl-2-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Phenyl-2-p-tolylpyrido[2,3-b]pyrazine (step 4) (179 mg, 0.602 mmol) under nitrogen in dry MeOH (5 ml) was treated with ammonium formate (190 mg, 3.01 mmol) and 10% palladium on carbon (64.1 mg, 0.060 mmol). The resulting mixture was heated at reflux for 16 hours. After cooling to RT, the mixture was filtered through Celite® (filter material) and the catalyst was washed with MeOH and MeOH/DCM (1:1). The filtrate was concentrated in vacuo and dissolved in DCM (50 ml). The solution was washed with water (×2) and brine (×1). The resulting organic portion was passed through a phase separating column and concentrated in vacuo to afford the title compound;

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 16 hours
  3. filtrationthe mixture was filtered through Celite® (filter material)
  4. washthe catalyst was washed with MeOH and MeOH/DCM (1:1)
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutiondissolved in DCM (50 ml)
  7. washThe solution was washed with water (×2) and brine (×1)
  8. customseparating column
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b894024fd86744e8a973313e9d5affa5
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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