Benzyl Alcohol → 6-(Benzyloxy)pyrazin-2-amine

HRID 1830765Notes

Reaction equation

HRID 1830765 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[NH2:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14](Cl)[N:13]=1>O1CCOCC1.C(OCC)(=O)C>[NH2:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:13]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 1184582-Amino-6-Chloropyrazine

Product 1

HCID 220464846-(Benzyloxy)pyrazin-2-amineYield 33%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of benzyl alcohol (432 μL; 4.0 mmol) in dioxane (2 mL) was added sodium hydride (96 mg; 4.0 mmol). After stirring for 30 minutes, 2-amino-6-chloropyrazine (258 mg; 2.0 mmol) was added and the reaction was heated to 90° C. After stirring for 12 hours, the reaction was cooled to room temperature, diluted with 30 mL of ethyl acetate and washed with aqueous 10% sodium carbonate (1×30 mL), and brine (30 mL), then dried (MgSO4) and filtered. The crude product was purified using the biotage 12i cartridge eluting with hexane and ethyl acetate (3:1) to yield a white solid (33% yield).

Workup

  1. stirringAfter stirring for 12 hours
  2. temperaturethe reaction was cooled to room temperature
  3. washwashed with aqueous 10% sodium carbonate (1×30 mL), and brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe crude product was purified
  7. washeluting with hexane and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-6c02a4f056c7443cba3cbaf26e6bb3da
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

Loading…