Methylamine → 3-Amino-6-bromo-N-methylpyrazine-2-carboxamide

HRID 646670Notes

Reaction equation

HRID 646670 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[CH3:13][NH2:14]>CO>[NH2:1][C:2]1[C:3]([C:9]([NH:14][CH3:13])=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylate

Product 1

HCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An ice-cooled solution of 50 g of methyl 3-amino-6-bromo-pyrazine-2-carboxylate in 500 mL of MeOH was saturated with methylamine gas. The reaction was then heated at 85° C. in a sealed, stainless steel Parr pressure vessel for 2 h, and cooled to room temperature, and then on an ice water bath. The mixture was concentrated to an oil on a rotary evaporator under reduced pressure. The crude oil was dissolved in EtOAc and washed with water, dried (Na2SO4), filtered, and concentrated to give 43.9 g (88.0% yield) of product as a solid.

Workup

  1. concentrationThe mixture was concentrated to an oil on a rotary evaporator under reduced pressure
  2. dissolutionThe crude oil was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-191d3358582b4750ba3d7caf849c8654
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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