2-Amino-5-bromopyrazine → 5-Methoxypyrazin-2-amine

HRID 556807Notes

Reaction equation

HRID 556807 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][O-:10].[Na+].CO>>[CH3:9][O:10][C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 5995392-Amino-5-bromopyrazineHCID 23694274Sodium methanolate methanol

Product 1

HCID 145364295-Methoxypyrazin-2-amineYield 32%

Conditions

Temperature
140 °C

Procedure

5-Bromopyrazin-2-amine (0.11 g, 0.63 mmol) was dissolved in NaOMe/MeOH (0.23 g Na metal in 10 mL MeOH) and heated by microwave irradiation at 140° C. for 7 hours. After evaporation of the solvent, the residue was purified by preparative TLC, eluting with 30% ethyl acetate-n-hexane, to give 5-methoxypyrazin-2-amine (25 mg, 32%).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by preparative TLC
  3. washeluting with 30% ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-ce0f03f5487641088c3f749e02f3b3bf
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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