Hydrochloric Acid → Methyl 3-fluoromethylpyrazine-2-carboxylate

HRID 2388628Notes

Reaction equation

HRID 2388628 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:9]([O:11][CH3:12])=[O:10])=[N:5][CH:6]=[CH:7][N:8]=1.[F-:13].[Cs+].Cl>CS(C)=O>[F:13][CH2:2][C:3]1[C:4]([C:9]([O:11][CH3:12])=[O:10])=[N:5][CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25953Cesium fluorideHCID 67039637Methyl 3-chloromethylpyrazine-2-carboxylate

Product 1

HCID 67039225Methyl 3-fluoromethylpyrazine-2-carboxylateYield 9.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

Methyl 3-chloromethylpyrazine-2-carboxylate (1.55 g, 8.3 mmol) was dissolved in DMSO (30 ml), followed by adding cesium fluoride (2.52 g, 16.6 mmol) and hexamethyl triamidophosphate (0.3 ml) and heated at 140° C. for 40 minutes while stirring. The reaction solution was cooled, followed by pouring into a diluted HCl solution, extracting with ethyl acetate, and washing with water. The solution was dried over magnesium sulfate, and concentrated under reduced pressure, and then the residue was purified by using silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 0.13 g of the desired compound.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionextracting with ethyl acetate
  3. washwashing with water
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified

Sources & evidence

ORD record
ord-6ee773351ce04e88bb96aa9523a258b1
Source dataset
uspto-grants-2012_09
Patent number
US08269045B2

Reaction notes

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