Pyridine → 2-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine

HRID 1034592Notes

Reaction equation

HRID 1034592 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.N1C=CC=CC=1.[Br:22]Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]([Br:22])=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 156743865-(4-Methoxyphenyl)pyrazin-2-amine

Product 1

HCID 715237102-Amino-3-bromo-5-(4-methoxyphenyl)pyrazineYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-amino-5-(4-mcthoxyphenyl)pyrazinc 16a (0.35 g, 1.7 mmol) and pyridine (0.20 mL, 2.6 mmol) in chloroform (20 mL), bromine (Br2) (0.13 mL, 2.6 mmol) was added dropwise in chloroform (3 mL) at −10° C. After 6 h stirring at room temperature, the reaction mixture was washed with water, the organic layer dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography using dichloromethane-EtOAc (90:10 v/v) as eluent, to obtain 0.33 g of 17a as an brown solid (mp 166-170° C., 70% yield). 1H-NMR (CDCl3): 3.83 (s, 3H), 5.04 (br s, 2H), 6.92-6.96 (m, 2H), 7.76-7.80 (m, 2H), 8.31 (s, 1H). GC-MS (EI): m/z 279,281 (M1, 100).

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialthe organic layer dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-fa0d033ad63b4d21ba822ff8ba9e0442
Source dataset
uspto-grants-2013_10
Patent number
US08546147B2

Reaction notes

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