Water → HCID 86707142, compound

HRID 57960Notes

Reaction equation

HRID 57960 reaction equation
Br[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH2:18])=[CH:13][CH:12]=1.CN1CCOCC1.O>CN1CCCC1=O>[Br:8][C:4]1[N:3]=[C:2]([NH:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:7]=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 754524-MethoxybenzylamineHCID 203617002,6-Dibromopyrazine

Product 1

HCID 86707142HCID 86707142, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,6-dibromopyrazine (3.431 mmol; 816.1 mg), (4-methoxyphenyl)methanamine (3.431 mmol; 470.6 mg; 0.4452 mL), and N-Methylmorpholine (8.577 mmol; 876 mg; 0.952 mL) in 1-methyl-2-pyrrolidinone (10 mL) in a sealed pressure vial was heated at 100° C. overnight. The mixture was poured into water, and extracted with EtOAc. The organic layer was concentrated. The residue was purified on silica eluted with 0 to 100% EtOAc in DCM to afford 6-bromo-N-[(4-methoxyphenyl)methyl]pyrazin-2-amine (768.8 mg, 29%).

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe organic layer was concentrated
  3. customThe residue was purified on silica
  4. washeluted with 0 to 100% EtOAc in DCM

Sources & evidence

ORD record
ord-3e9c5780a12b40f7b565b93b3e01dbfa
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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