Methanol → tert-Butyl 8-methoxy-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 2276604Notes

Reaction equation

HRID 2276604 reaction equation
Br[CH:2]1[C:11]2[C:6](=[N:7][C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=2)[N:5]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:4][CH2:3]1.[CH3:31][OH:32]>C(=O)([O-])[O-].[Ag+2]>[CH3:31][O:32][CH:2]1[C:11]2[C:6](=[N:7][C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=2)[N:5]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 66666005tert-Butyl 8-bromo-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate2×

Product 1

HCID 66665716tert-Butyl 8-methoxy-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Reagents, catalysts & solvents 1

HCID 178418647HCID 178418647, compoundCatalyst

Procedure

To a solution of tert-butyl 8-bromo-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (Intermediate H) (200 mg, 0.429 mmol) in dry MeOH (8 ml, 198 mmol) was added silver carbonate (237 mg, 0.858 mmol). The mixture was stirred at RT for 2.5 hours under nitrogen and then filtered through Celite® (filter material) washing through with methanol (25 ml). The filtrate was concentrated in vacuo to afford the title compound;

Workup

  1. filtrationfiltered through Celite® (filter material)
  2. washwashing through with methanol (25 ml)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2d63a1fbcfd84c0aabce4f59e195c28d
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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