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

HRID 1842204Notes

Reaction equation

HRID 1842204 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-f24baad0bd2b4d86aeffac85d48e5e1a
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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