Water → Methyl 5-(((allyloxy)carbonyl)amino)pyrazine-2-carboxylate

HRID 2192914Notes

Reaction equation

HRID 2192914 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20].O>ClCCl>[CH2:22]([O:21][C:19]([NH:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1)=[O:20])[CH:23]=[CH2:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 18052Allyl chloroformateHCID 14536427Methyl 5-aminopyrazine-2-carboxylate

Product 1

HCID 59570895Methyl 5-(((allyloxy)carbonyl)amino)pyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-aminopyrazine-2-carboxylate (2 g) in dichloromethane (20 mL) were added pyridine (36.4 mL) and allyl chloroformate (25.2 mL) in 4 divided portions respectively, under ice-cooling, followed by stirring at room temperature overnight. To the reaction mixture was added water under ice-cooling, followed by extraction with ethyl acetate. The organic layer was sequentially washed with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained solid was collected by filtration while washing with a solvent (hexane:ethyl acetate=3:1) to obtain methyl 5-{[(allyloxy)carbonyl]amino}pyrazine-2-carboxylate (481 mg) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was sequentially washed with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. filtrationThe obtained solid was collected by filtration
  8. washwhile washing with a solvent (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-5f0e2b42efed48c28445b77afe091370
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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