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

HRID 1296608Notes

Reaction equation

HRID 1296608 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-16a55b5b94134911aa39022981d4cbcc
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

Loading…