2-Pyrrolidone → 1-(3-Chloropyrazin-2-yl)pyrrolidin-2-one

HRID 645794Notes

Reaction equation

HRID 645794 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[Cl:9][C:10]1[C:15](Cl)=[N:14][CH:13]=[CH:12][N:11]=1>CN(C)C=O>[Cl:9][C:10]1[C:15]([N:3]2[CH2:7][CH2:6][CH2:5][C:4]2=[O:8])=[N:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 785752,3-Dichloropyrazine

Product 1

HCID 532497151-(3-Chloropyrazin-2-yl)pyrrolidin-2-oneYield 32.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% in mineral oil, 67 mg, 1.62 mmol) was added to a solution of pyrrolidinone (0.12 ml, 1.54 mmol) in dry dimethylformamide (5 ml) under argon at 0° C. The mixture was allowed to warm to room temperature over 1.5 hours. A solution of 2,3-dichloropyrazine (D46, Step 2) (250 mg, 1.69 mmol) in dry dimethylformamide (2 ml) was added and the mixture stirred at room temperature under argon for 2 hours. The mixture was poured onto water (30 ml) and was extracted with ethyl acetate (×3). The ethyl acetate extracts were combined, washed with brine, dried under magnesium sulfate and evaporated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ethyl acetate:pentane (1:1) to afford the title compound (0.10 g); MS (ES+) m/e 198 [M+H]+.

Workup

  1. additionThe mixture was poured onto water (30 ml)
  2. extractionwas extracted with ethyl acetate (×3)
  3. washwashed with brine
  4. customdried under magnesium sulfate
  5. customevaporated in vacuo
  6. customThe resulting residue was purified by column chromatography
  7. washeluting with a mixture of ethyl acetate:pentane (1:1)

Sources & evidence

ORD record
ord-2c570ecde0e14249a015e1bec00a9fc3
Source dataset
uspto-grants-2010_04
Patent number
US07704994B2

Reaction notes

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