Ammonia → HCID 58328514, compound

HRID 1844535Notes

Reaction equation

HRID 1844535 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.[NH2:13][C:14]1[CH:19]=[N:18][C:17](Br)=[CH:16][N:15]=1.N>[Cu].O>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][O:10][C:17]2[N:18]=[CH:19][C:14]([NH2:13])=[N:15][CH:16]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 5995392-Amino-5-bromopyrazine

Product 1

HCID 58328514HCID 58328514, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

Sodium hydride (60% oily product) (78.8 mg) was added to 4-methoxybenzyl alcohol (2.14 mL) at a room temperature in an argon atmosphere, and the mixture was stirred for 30 minutes under the same conditions. Next, the reaction mixture was transferred to a metal seal tube. A copper powder (146 mg) and 2-amino-5-bromopyrazine (300 mg) were added, and the resultant mixture was heated and stirred at 160° C. for about 6 hours. After cooling, 25% aqueous ammonia and water were poured into the reaction solution. The reaction mixture was stirred for 1 hour at room temperature, and then filtrated through Celite. Water (20 mL) was added to the filtrate, and the resultant mixture was extracted with ethyl acetate (20 mL×3). The organic layer was washed with saturated brine (50 mL). The washed organic layer was dried over anhydrous sodium sulfate and filtrated, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=3:1) to give 5-(4-methoxybenzyloxy)pyrazin-2-amine (104 mg).

Workup

  1. customseal tube
  2. stirringstirred at 160° C. for about 6 hours
  3. temperatureAfter cooling
  4. stirringThe reaction mixture was stirred for 1 hour at room temperature
  5. filtrationfiltrated through Celite
  6. additionWater (20 mL) was added to the filtrate
  7. extractionthe resultant mixture was extracted with ethyl acetate (20 mL×3)
  8. washThe organic layer was washed with saturated brine (50 mL)
  9. dry with materialThe washed organic layer was dried over anhydrous sodium sulfate
  10. filtrationfiltrated
  11. customthe solvent was removed under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-d5c4ee1dd3cb43f197541177c5182a47
Source dataset
uspto-grants-2015_02
Patent number
US08946440B2

Reaction notes

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