Sodium Chloride → t-Butyl 5-methylpyrazine-2-carboxylate

HRID 1693172Notes

Reaction equation

HRID 1693172 reaction equation
[CH3:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.ClC(Cl)(Cl)C(=N)O[C:15]([CH3:18])([CH3:17])[CH3:16].[Cl-].[Na+].C(OCC)(=O)C>O1CCCC1>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 1228315-Methyl-2-pyrazinecarboxylic acidHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate

Product 1

HCID 57475683t-Butyl 5-methylpyrazine-2-carboxylateYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A boron trifluoride-diethyl ether complex (91.7 μL) was added dropwise to a suspension of 2-methylpyrazine-5-carboxylic acid (1 g) and tert-butyl 2,2,2-trichloroacetimidate (4.75 g) in tetrahydrofuran (20 mL) under ice-cooling. The reaction solution was warmed to room temperature, followed by stirring for two hours. A saturated sodium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated and purified by silica gel column chromatography to obtain the title compound (1.4 g).

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe insoluble matter was separated by filtration
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-6b3ae6c3b0d64d1b9b60c0589847da86
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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