Trifluoroacetic acid → 5-[2-(Benzyloxy)ethoxy]pyrazin-2-amine

HRID 2192913Notes

Reaction equation

HRID 2192913 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[N:13]=[CH:14][C:15]([NH:18]C(=O)OC(C)(C)C)=[N:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[N:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59570995Tert-butyl {5-[2-(benzyloxy)ethoxy]pyrazin-2-yl}carbamate

Product 1

HCID 595709315-[2-(Benzyloxy)ethoxy]pyrazin-2-amineYield 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {5-[2-(benzyloxy)ethoxy]pyrazin-2-yl}carbamate (614 mg) in dichloromethane (10 mL) was added trifluoroacetic acid (0.68 mL) at room temperature, followed by stirring at room temperature overnight. After concentration, saturated aqueous sodium bicarbonate was added thereto. After extraction with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate. The crude product obtained by concentration was purified by basic silica gel column chromatography (hexane:ethyl acetate=5:1-1:1) to obtain 5-[2-(benzyloxy)ethoxy]pyrazin-2-amine (269 mg) as a pale yellow solid.

Workup

  1. concentrationAfter concentration, saturated aqueous sodium bicarbonate
  2. additionwas added
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe crude product obtained by concentration
  6. customwas purified by basic silica gel column chromatography (hexane:ethyl acetate=5:1-1:1)

Sources & evidence

ORD record
ord-36031c5d59554fac93876b37a39d7f57
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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