Boron trifluoride etherate → Methyl 5-aminopyrazine-2-carboxylate

HRID 1639928Notes

Reaction equation

HRID 1639928 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]#N)=[N:6][CH:7]=1.B(F)(F)F.CC[O:16][CH2:17]C.C([O-])(O)=[O:20].[Na+]>CO>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:16][CH3:17])=[O:20])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 139252945-Aminopyrazine-2-carbonitrile

Product 1

HCID 14536427Methyl 5-aminopyrazine-2-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reflux a solution of 2.24 g (18.65 mmol) of 5-aminopyrazine-2-carbonitrile and 9.45 mL (74.40 mmol) of boron trifluoride etherate in 50 mL of methanol for 2 h. Concentrate the reaction mixture under reduced pressure and take up the residue obtained in 200 mL of EtOAc and 10 mL of a saturated aqueous solution of NaHCO3. Dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a cyclohexane/EtOAc 1:1 mixture. After concentration under reduced pressure, we obtain 1.4 g of methyl 5-aminopyrazine-2-carboxylate in the form of oil.

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. customobtained in 200 mL of EtOAc
  3. dry with materialDry the organic phase over Na2SO4
  4. concentrationconcentrate under reduced pressure
  5. customPurify the residue
  6. customobtained by silica gel column chromatography
  7. washeluting with a cyclohexane/EtOAc 1:1 mixture
  8. concentrationAfter concentration under reduced pressure, we

Sources & evidence

ORD record
ord-f36b349f8cd249bf892bb0210a392c2c
Source dataset
uspto-grants-2012_02
Patent number
US08110579B2

Reaction notes

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