Water → tert-Butyl (5-formylpyrazin-2-yl)carbamate

HRID 385609Notes

Reaction equation

HRID 385609 reaction equation
Br[CH2:2][C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1.O.O.C[N+]([O-:23])(C)C.O.C(Cl)(Cl)Cl>CS(C)=O.ClCCl>[CH:2]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1)=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 198430Trimethylamine oxide dihydrateHCID 45073740tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

Product 1

HCID 44118835tert-Butyl (5-formylpyrazin-2-yl)carbamateYield 75.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixed solution of 0.17 g of tert-butyl (5-(bromomethyl)pyrazin-2-yl)carbamate in 4 mL of dimethyl sulfoxide and 2 mL of dichloromethane, 0.26 g of trimethylamine N-oxide dihydrate was added under cooling with ice, and the mixture was stirred for 2 hours. Thereto were added water and chloroform, the organic layer was separated, and washed with a saturated aqueous sodium hydrogen carbonate solution, water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.10 g of tert-butyl (5-formylpyrazin-2-yl)carbamate as a white solid.

Workup

  1. temperatureunder cooling with ice
  2. customthe organic layer was separated
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution, water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-db6e074454a145b28dd28dcb5a3fcc26
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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