3-Aminopyridine → 5-Bromo-1-methyl-3-(pyridin-3-ylamino)pyrazin-2(1H)-one

HRID 592775Notes

Reaction equation

HRID 592775 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.Br[C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13]([Br:15])[N:14]=1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[Br:15][C:13]1[N:14]=[C:9]([NH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=1

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

Product 1

HCID 666133725-Bromo-1-methyl-3-(pyridin-3-ylamino)pyrazin-2(1H)-oneYield 50%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with pyridin-3-amine (940 mg, 10 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (5.4 g, 20 mmol), i-propanol (50 mL), and di-i-propylethylamine (10 mL). The mixture was heated at reflux for 5 h. After the completion of the reaction, it was cooled to room temperature. The solvent was removed under reduced pressure. The crude was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 186a (1.4 g, 50%) as a yellow solid. MS-ESI: [M+H]+ 281.6.

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 5 h
  4. customAfter the completion of the reaction, it
  5. customThe solvent was removed under reduced pressure
  6. customThe crude was purified by silica-gel column chromatography
  7. washeluting with 30:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-af5a8bd535fd475c91b872b836fe8b37
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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