Water → 2-Chloro-6-[(3-methoxybenzyl)oxy]pyrazine

HRID 1357567Notes

Reaction equation

HRID 1357567 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][OH:15].[H-].[Na+].O>O1CCOCC1.C(OCC)(=O)C>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([O:10][CH3:9])[CH:12]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 814373-Methoxybenzyl alcohol

Product 1

HCID 181869202-Chloro-6-[(3-methoxybenzyl)oxy]pyrazineYield 114.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,6-dichloropyrazine (444 mg, 3.00 mmol) and 3-methoxybenzyl alcohol (455 mg, 3.30 mmol) in dioxane (5 mL) was added NaH (55% in oil, 144 mg, 3.30 mmol) at room temperature. The reaction mixture was stirred overnight. Water (0.5 mL) and ethyl acetate (10 mL) were added and the mixture was stirred for 15 min and then filtered. The filtrate was dried over K2CO3 and concentrated to give an oil (0.86 g) that was used directly in the next step. MS m/z 250 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. filtrationfiltered
  3. dry with materialThe filtrate was dried over K2CO3
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3fe5a9038a3a4804adf136887f714651
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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