HCID 66665855, compound → rac-7-Methoxy-2,3-dip-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

HRID 406270Notes

Reaction equation

HRID 406270 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[N:25][C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=[C:5]2[CH:4]=1>CO.[Pd]>[CH3:1][O:2][CH:3]1[CH2:26][NH:25][C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)[N:10]=[C:5]2[CH2:4]1

Participants

4

Reactant 1

HCID 66665855HCID 66665855, compound

Product 1

HCID 66665854rac-7-Methoxy-2,3-dip-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

7-Methoxy-2,3-dip-tolylpyrido[2,3-b]pyrazine (94 mg, 0.275 mmol) in dry MeOH (4 ml), under nitrogen was treated with 10% Pd on Carbon (58.6 mg, 0.056 mmol). The suspension was stirred at RT under an atmosphere of hydrogen for 32 hours. The resulting mixture was loaded onto a 2.5 g Celite® column using MeOH and was flushed with 1:1 MeOH:DCM. The filtrate was concentrated in vacuo and the residue was dissolved in DCM (30 ml) and washed with water (×2). The organic portion was isolated and the solvent was removed in vacuo to afford the title compound; LCMS Rt 1.12 mins MS m/z 346 [ M+H]+ Method 2minLC_v003

Workup

  1. customwas flushed with 1:1 MeOH
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe residue was dissolved in DCM (30 ml)
  4. washwashed with water (×2)
  5. customThe organic portion was isolated
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0d52547f73124ca7b00687ca98a020c4
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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