Potassium Carbonate → Methyl 5-(cyclopropoxy)pyrazine-2-carboxylate

HRID 571742Notes

Reaction equation

HRID 571742 reaction equation
[CH:1]1([OH:4])[CH2:3][CH2:2]1.Cl[C:6]1[N:7]=[CH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[N:10][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH:1]1([O:4][C:6]2[N:7]=[CH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[N:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123361CyclopropanolHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 117738401Methyl 5-(cyclopropoxy)pyrazine-2-carboxylateYield 54.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Cyclopropanol (542 μL, 8.69 mmol) is added to a suspension of methyl 5-chloropyrazine-2-carboxylate (1.0 g, 5.79 mmol) and potassium carbonate (1.60 g, 11.59 mmol) in dimethylformamide (11.6 mL). The reaction mixture is stirred for 15 hours at room temperature then for 24 hours at 50° C. The reaction is cooled to ambient temperature, diluted with water, and extracted with ethyl acetate (3 times). The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a brown oil. The crude product is purified by silica gel flash chromatography, eluting with ethyl acetate/hexane (0:100) to ethyl acetate/hexane (35:65) to give the title compound (610 mg, 54%). ES/MS (m/e): 195.0 (M+1).

Workup

  1. waitfor 24 hours at 50° C
  2. temperatureThe reaction is cooled to ambient temperature
  3. extractionextracted with ethyl acetate (3 times)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a brown oil
  8. customThe crude product is purified by silica gel flash chromatography
  9. washeluting with ethyl acetate/hexane (0:100) to ethyl acetate/hexane (35:65)

Sources & evidence

ORD record
ord-389b598e309443e7bd19ecc4b49d6c07
Source dataset
uspto-grants-2015_05
Patent number
US09029367B2

Reaction notes

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