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

HRID 2045859Notes

Reaction equation

HRID 2045859 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].[Na+].[Cl-].CCOC(C)=O>C1COCC1>[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 THF (20 mL) under ice-cooling. The reaction solution was warmed to RT, followed by stirring for 2 h. A saturated NaCl solution and EtOAc were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous MgSO4, 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). 1H-NMR (CDCl3) δ (ppm): 1.65 (s, 9H), 2.65 (s, 3H), 8.57 (d, J=1.2 Hz, 1H), 9.10 (d, J=1.6 Hz, 1H).

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  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-9c40b3a475b5446f85a87a8eafa8e70a
Source dataset
uspto-grants-2013_11
Patent number
US08592408B2

Reaction notes

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