Methyl 3-aminopyrazinecarboxylate → Methyl 3-amino-6-iodopyrazine-2-carboxylate

HRID 334383Notes

Reaction equation

HRID 334383 reaction equation
[I:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:11]([C:16]([O:18][CH3:19])=[O:17])=[N:12][CH:13]=[CH:14][N:15]=1>CN(C)C=O>[NH2:9][C:10]1[C:11]([C:16]([O:18][CH3:19])=[O:17])=[N:12][C:13]([I:1])=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 72669Methyl 3-aminopyrazinecarboxylateHCID 120273N-Iodosuccinimide2×

Product 1

HCID 11087124Methyl 3-amino-6-iodopyrazine-2-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide. The reaction medium is heated at 65° C. for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65° C. for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10% sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88%) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid.

Workup

  1. temperaturemaintained at 65° C. for 24 hours
  2. customAfter returning to room temperature
  3. customthe solvent is evaporated
  4. extractionthe product is extracted several times with dichloromethane
  5. washwashed with 10% sodium bisulfite solution
  6. customdried on magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6ff15b6de6a441d9bc4c3f8a1eb0123a
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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