Sodium hydride → 2-Chloro-6-(6-fluoro-pyridin-2-ylmethoxy)-pyrazine

HRID 2182138Notes

Reaction equation

HRID 2182138 reaction equation
[F:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=1.[H-].[Na+]>C1COCC1>[Cl:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13]([O:9][CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=2)[N:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 12045263(6-Fluoropyridin-2-yl)methanol

Product 1

HCID 224820092-Chloro-6-(6-fluoro-pyridin-2-ylmethoxy)-pyrazineYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-fluoro-pyridin-2-yl)-methanol I-3d (368 mg, 2.89 mmol) and 2,6-dichloro-pyrazine (431.2 mg, 2.89 mM) in THF (14.7 mL) at room temperature was added 60% NaH in mineral oil (174 mg, 4.34 mmol). The resulting mixture was stirred at ambient temperature for 19 h and concentrated. The residue was purified by column chromatography (ethyl acetate/hexanes=1:4)) to afford 560 mg of the title compound (I-3e).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography (ethyl acetate/hexanes=1:4))

Sources & evidence

ORD record
ord-903df2787c7c485ea7e847ceec5bab17
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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