Ethyl Acetate → HCID 86647482, compound

HRID 2192898Notes

Reaction equation

HRID 2192898 reaction equation
C(OC([NH:8][C:9]1[N:10]=[CH:11][C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N:13][CH:14]=1)=O)(C)(C)C.O1CCOCC1.Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCOCC1.O.[Cl-].[Na+].O>[NH2:8][C:9]1[N:10]=[CH:11][C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N:13][CH:14]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 86647483HCID 86647483, compound

Product 1

HCID 86647482HCID 86647482, compoundYield 88.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of methyl {5-[(tert-butoxycarbonyl)amino]pyrazin-2-yl}acetate (0.4811 g) in dioxane (5 mL) was added a 4 M hydrogen chloride dioxane solution (5 mL), followed by stirring overnight. The reaction mixture was concentrated and the obtained crude product was collected by filtration and washed with ethyl acetate. The obtained crude product was dissolved in water, and saturated aqueous sodium bicarbonate and ethyl acetate were added thereto, followed by stirring for 1 hour. Saturated brine was added thereto, followed by extraction with ethyl acetate (10 mL×20 times), and the obtained organic layer was washed with saturated brine, dried using anhydrous magnesium sulfate. After concentration under reduced pressure, methyl (5-aminopyrazin-2-yl)acetate (0.2662 g) was obtained as a pale yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe obtained crude product
  3. filtrationwas collected by filtration
  4. washwashed with ethyl acetate
  5. customThe obtained crude product
  6. stirringby stirring for 1 hour
  7. extractionfollowed by extraction with ethyl acetate (10 mL×20 times)
  8. washthe obtained organic layer was washed with saturated brine
  9. customdried
  10. concentrationAfter concentration under reduced pressure

Sources & evidence

ORD record
ord-1252b60c73f64e14bb09a3d193980d5f
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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