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

HRID 2242902Notes

Reaction equation

HRID 2242902 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]>>[CH3:13][NH:14][C:9]([C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([Br:8])[N:4]=1)=[O:11]

Participants

3

Reactant 2

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

Product 1

HCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamideYield 90%

Procedure

Methyl 3-amino-6-bromo-2-pyrazine-carboxylate (14.3 g, 61.6 mmol; see Example 16 (a) above) was suspended in 40% aqueous methylamine (350 mL) and the resulting mixture was stirred vigorously for 7 hours at room temperature. The precipitate was collected, washed with water, and dried to afford 3-amino-6-bromo-pyrazine-2-carboxylic acid methylamide as a yellow solid (12.7 g, 90%). 1H NMR (300 MHz, DMSO-d6) δ2.77 (d, J=3 Hz, 3H), 7.70 (br s, 2H), 8.33 (s, 1H), 8.56 (q, J=3 Hz, 1 H); 13C NMR (100 MHz, DMSO-d6) δ27.84, 123.49, 127.69, 150.43, 156.04, 167.18.

Workup

  1. customThe precipitate was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-c5f91e4ad45646cdb4f668e9b4d38eac
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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