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Sodium hydride → 1-(5,6-Diphenylpyrazin-2-yloxy)-4-(2-tetrahydropyranyloxy)butane

HRID 1271308
Notes
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Reaction equation

HRID 1271308 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[H-].[Na+].Cl[C:16]1[N:17]=[C:18]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:20][CH:21]=1>O1CCCC1>[C:28]1([C:18]2[N:17]=[CH:16][C:21]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[N:20][C:19]=2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5591134-(Tetrahydro-2H-pyran-2-yloxy)-1-butanolHCID 36544935-Chloro-2,3-Diphenylpyrazine

Product 1

HCID 229319531-(5,6-Diphenylpyrazin-2-yloxy)-4-(2-tetrahydropyranyloxy)butaneYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.57 g of 4-(2-tetrahydropyranyloxy)-1-butanol was dissolved in 20 ml of tetrahydrofuran and 360 mg of 60% sodium hydride was added under ice cooling, followed by stirring at room temperature for 1.5 hours. The mixture was refluxed for 30 minutes and ice-cooled again and 2.00 g of 5-chloro-2,3-diphenylpyrazine was added. After stirring for 40 minutes, the mixture was heated to 80° C., stirred at the same temperature for 4.5 hours and then stirred at room temperature for 88 hours. The reaction solution was combined with ice water, extracted with ethyl acetate and then washed with saturated brine. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain 2.39 g of the desired compound as an oily substance.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperatureice-cooled again
  3. stirringAfter stirring for 40 minutes
  4. temperaturethe mixture was heated to 80° C.
  5. stirringstirred at the same temperature for 4.5 hours
  6. stirringstirred at room temperature for 88 hours
  7. extractionextracted with ethyl acetate
  8. washwashed with saturated brine
  9. dry with materialThe extract was dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a3f7b7c9258a4c8c9ff5fd0813d02542
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07205302B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes