1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-Butyl 2,3-diphenylpyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 406264Notes

Reaction equation

HRID 406264 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.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[C:12]1([C:9]2[N:10]=[C:11]3[CH:2]=[CH:3][CH2:4][N:5]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:6]3=[N:7][C:8]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66666005tert-Butyl 8-bromo-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate2×

Product 1

HCID 66665728tert-Butyl 2,3-diphenylpyrido[2,3-b]pyrazine-5(6H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-Butyl 8-bromo-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (Intermediate H) (5 g, 10.72 mmol) in DCM (250 ml) was treated with DBU (1.939 ml, 12.87 mmol) and was stirred at RT under an atmosphere of nitrogen overnight. The solvent was removed in vacuo. The resulting crude product was purified by chromatography on silica eluting with 0-20% EtOAc/iso-hexane to afford the title compound;

Workup

  1. customThe solvent was removed in vacuo
  2. customThe resulting crude product was purified by chromatography on silica eluting with 0-20% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-38750f723b0b453597ad1ac33bd951d1
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

Loading…