2-Methylbenzyl alcohol → 2-Amino-3-(2-methylbenzyloxy)pyrazine

HRID 4293

Reaction equation

HRID 4293 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[H-].[Na+].[NH2:12][C:13]1[C:18](Cl)=[N:17][CH:16]=[CH:15][N:14]=1>CN(C)C=O>[NH2:12][C:13]1[C:18]([O:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[CH3:1])=[N:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 69942-Methylbenzyl alcoholHCID 24758Sodium hydrideHCID 2762242-Amino-3-chloropyrazine

Product 1

HCID 138259752-Amino-3-(2-methylbenzyloxy)pyrazineYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2-methylbenzyl alcohol (0.985 g) in N,N-dimethylformamide (10 ml) was added 62.8% sodium hydride (0.308 g) under a nitrogen atmosphere and then stirred for 30 minutes. 2-Amino-3-chloropyrazine (0.87 g) was added to the solution and the mixture was heated at 65° C. for 2 hours and poured onto crushed ice. The resulting precipitates were collected by filtration, washed with n-hexane, and dried in a desiccator to give 2-amino-3-(2-methylbenzyloxy)pyrazine (0.6 g).

Workup

  1. additionpoured
  2. customonto crushed ice
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with n-hexane
  6. customdried in a desiccator

Sources & evidence

ORD record
ord-163ac3e349334314939c73ed51b57929
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Linked notes

Loading…