Isopropanol → 2-Chloro-6-[(propan-2-yl)oxy]pyrazine

HRID 1529308Notes

Reaction equation

HRID 1529308 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].[H-].[Na+].[Cl:7][C:8]1[CH:13]=[N:12][CH:11]=[C:10](Cl)[N:9]=1>C1COCC1>[Cl:7][C:8]1[CH:13]=[N:12][CH:11]=[C:10]([O:4][CH:2]([CH3:3])[CH3:1])[N:9]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

Product 1

HCID 246891122-Chloro-6-[(propan-2-yl)oxy]pyrazineYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of IPA (50.0 g, 0.369 mol) in 500 mL of THF slowly was added 60% NaH (27.0 g, 0.671 mol) at RT under N2 atmosphere and stirred at RT for 20 min. Then the reaction mixture was slowly treated with 2,6-dichloropyrazine (50 g, 0.336 mol) at RT and stirred at RT for 1 h. The resulting mixture was poured into ice water and extracted with EtOAc. The organic layer was separated, dried over anhydrous Na2SO4, and concentrated to afford crude 2-chloro-6-isopropoxypyrazine (53 g) as pale brown liquid. This material was used further step without purification. MS (ESI, m/z): 173 (M+1).

Workup

  1. stirringstirred at RT for 1 h
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0e60022de3b849dd83469143ba6bacfe
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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