Sodium Hydroxide → 2,3-Dip-tolyl-5,6-dihydropyrido[2,3-b]pyrazine

HRID 406199Notes

Reaction equation

HRID 406199 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([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:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH:23]=[CH: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:3][CH:2]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 666645252,3-Di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine2×

Product 1

HCID 666660012,3-Dip-tolyl-5,6-dihydropyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 2,3-Dip-tolylpyrido[2,3-b]pyrazine (Intermediate E, step 1) (6.74 g, 21.65 mmol) in THF (130 ml) was added dropwise at room temperature 2.4 M LiAlH4 in THF (4.51 ml, 10.82 mmol). To the reaction mixture cooled to 0° C. was added dropwise and successively water (0.409 ml), 15% aqueous NaOH (0.409 ml) and water (1.227 ml). The mixture was stirred at 0° C. for 15 min and allowed to warm to RT. Anhydrous MgSO4 was added and the mixture was stirred for 15 min and filtered. The residue was washed with EtOAc (×5) and the filtrate was concentrated in vacuo to afford the title compound:

Workup

  1. additionwas added dropwise
  2. temperatureto warm to RT
  3. stirringthe mixture was stirred for 15 min
  4. filtrationfiltered
  5. washThe residue was washed with EtOAc (×5)
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2384b459f78841ca8abf799646c47b48
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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