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

HRID 2276598Notes

Reaction equation

HRID 2276598 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[CH:23]=[CH:22][CH:21]=[N:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[C:1]1([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][NH:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 666655042-Phenyl-3-p-tolyl-pyrido[2,3-b]pyrazine

Product 1

HCID 666662562-Phenyl-3-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

2-Phenyl-3-p-tolyl-pyrido[2,3-b]pyrazine (1.07 g, 3.60 mmol) under nitrogen in dry MeOH (10 ml) was treated with ammonium formate (2.269 g, 36.0 mmol) and 10% palladium hydroxide on carbon (200 mg, 0.142 mmol). The resulting mixture was heated at reflux for 1 hour. After cooling to RT, the mixture was filtered through Celite® (filter material) and the catalyst was washed with MeOH followed by DCM. The filtrate was concentrated in vacuo to yield a solid which was triturated with MeOH. The resulting solid was dried under vacuum to afford the title compound;

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1 hour
  3. filtrationthe mixture was filtered through Celite® (filter material)
  4. washthe catalyst was washed with MeOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto yield a solid which
  7. customwas triturated with MeOH
  8. customThe resulting solid was dried under vacuum

Sources & evidence

ORD record
ord-db08ffa3d0024b61ad59314aa5da8f64
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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