Benzyl Alcohol → 3-(Benzyloxy)-5-bromopyrazin-2-amine

HRID 2174652Notes

Reaction equation

HRID 2174652 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[C:12]1[C:13]([NH2:19])=[N:14][CH:15]=[C:16]([Br:18])[N:17]=1>C1COCC1>[CH2:3]([O:10][C:12]1[C:13]([NH2:19])=[N:14][CH:15]=[C:16]([Br:18])[N:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 6200042-Amino-3,5-dibromopyrazine

Product 1

HCID 107551623-(Benzyloxy)-5-bromopyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH as a 60% dispersion in mineral oil (31.63 mg, 0.7908 mmol) was added to a solution of benzyl alcohol (85.52 mg, 81.84 μL, 0.7908 mmol) in THF (4 mL). After stirring at ambient temperature for 5 minutes, 3,5-dibromopyrazin-2-amine (100 mg, 0.3954 mmol) was added and the mixture was stirred for 1 hour at ambient temperature then heated at 80° C. under microwave conditions for 15 minutes. The reaction mixture was cooled to ambient temperature, concentrated in vacuo and used directly in the next step without further purification.

Workup

  1. stirringthe mixture was stirred for 1 hour at ambient temperature
  2. temperaturethen heated at 80° C. under microwave conditions for 15 minutes
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. concentrationconcentrated in vacuo
  5. customused directly in the next step without further purification

Sources & evidence

ORD record
ord-8cd361a627474468b542bca9bcb480ec
Source dataset
uspto-grants-2015_06
Patent number
US09062008B2

Reaction notes

Loading…