Pyrazine, 2-(chloromethyl)- → HCID 54520121, compound

HRID 2203401Notes

Reaction equation

HRID 2203401 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1.[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K]>CN(C)C=O>[N:4]1[CH:5]=[CH:6][N:7]=[CH:8][C:3]=1[CH2:2][N:13]1[C:9](=[O:19])[C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]1=[O:14]

Participants

4

Reactant 2

HCID 170169Pyrazine, 2-(chloromethyl)-HCID 24194345Phthalimide potassium salt

Product 1

HCID 54520121HCID 54520121, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-(chloromethyl)pyrazine (2.63 g, 20.5 mmol) (prepared according to Zhang, X.-A. et al., J. Am. Chem. Soc. 2008, 130, 15788-15789) in N,N-dimethylformamide (20 mL) was added potassium phthalimide (3.98 g, 21.5 mmol). The reaction mixture was heated for 16 h at 110° C., allowed to cool to ambient temperature and concentrated in vacuo. The residue was partitioned between dichloromethane (150 mL) and water (50 mL). The organic phase was washed with water (50 mL) and brine (2×20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated in a mixture of ethyl acetate and hexanes (1:1) to afford 2-(pyrazin-2-ylmethyl)isoindoline-1,3-dione as a light brown solid in 73% yield (3.56 g): 1H NMR (300 MHz, CDCl3) δ8.63 (s, 1H), 8.45 (s, 2H), 7.89-7.83 (m, 2H), 7.76-7.70 (m, 2H), 5.03 (s, 2H); MS (ES+) m/z 240.0 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (150 mL) and water (50 mL)
  4. washThe organic phase was washed with water (50 mL) and brine (2×20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated in a mixture of ethyl acetate and hexanes (1:1)

Sources & evidence

ORD record
ord-7d7b37697b0c4f5e90e585ad6c1f0788
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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