Bromine → Methyl 3-Amino-6-bromopyrazine-2-carboxylate

HRID 2242901Notes

Reaction equation

HRID 2242901 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[Br:12]Br>C(O)(=O)C.O>[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][C:5]([Br:12])=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 72669Methyl 3-aminopyrazinecarboxylate

Product 1

HCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Methyl 3-amino-2-pyrazine-carboxylate (10 g, 65.3 mmol) was dissolved in glacial acetic acid (50 mL) by warming to approximately 45° C. To the warm solution was added bromine (3.7 mL) in acetic acid (5 mL) dropwise and the resulting mixture was stirred at room temperature for 20 minutes. The solution was diluted with water (300 mL) and then stirred at room temperature for 30 minutes, which resulted in a precipitate. The precipitate was then filtered, washed with water and dried to afford methyl 3-amino-6-bromo-2-pyrazine-carboxylate as a yellow solid (14.2 g, 94%). 1H NMR (300 MHz, CDCl3) δ3.99 (s, 3H), 8.30 (s, 1 H); 13C NMR (100 MHz, CDCl3) δ 53.02, 123.49, 124.85, 150.24, 154.70, 166.04.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. customwhich resulted in a precipitate
  3. filtrationThe precipitate was then filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-de767317d2b64745a5046157ac617a69
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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