Water → 2-Chloro-6-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazine

HRID 2188694Notes

Reaction equation

HRID 2188694 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH3:9][O:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:13]2[CH2:14][CH2:15][CH2:16][CH:12]2[CH2:11][O:10][CH3:9])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 785042,6-DichloropyrazineHCID 1439532-(Methoxymethyl)pyrrolidine

Product 1

HCID 866490092-Chloro-6-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazineYield 80.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2,6-dichloropyrazine (1.18 g), 2-(methoxymethyl)pyrrolidine (1.0 g) and potassium carbonate (1.64 g) in DMA (15 mL) was stirred at 80° C. for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient: 5→15% ethyl acetate/hexane) to give the title compound (1.45 g, 80%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent gradient: 5→15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e37acd0a11dd43a195fab14c0a2319da
Source dataset
uspto-grants-2012_12
Patent number
US08324201B2

Reaction notes

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