5,6-Diphenyl-2-(5-hydroxy-1-pentyn-1-yl)pyrazine → 5,6-Diphenyl-2-(5-hydroxypentan-1-yl)pyrazine

HRID 1271303Notes

Reaction equation

HRID 1271303 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][OH:24])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[C].[Pd]>[C:1]1([C:7]2[N:8]=[CH:9][C:10]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 229319465,6-Diphenyl-2-(5-hydroxy-1-pentyn-1-yl)pyrazine

Product 1

HCID 229320225,6-Diphenyl-2-(5-hydroxypentan-1-yl)pyrazineYield 98.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 400 mg of 5,6-diphenyl-2-(5-hydroxy-1-pentyn-1-yl)pyrazine in 20 ml of ethanol, 80 mg of 5% palladium-carbon was added and the mixture was hydrogenated at 30° C. for 5 hours. After 40 mg of 5% palladium-carbon was further added, hydrogenation was continued for one hour. The catalyst was removed by filtering the reaction solution through celite and the filtrate was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 398 mg of the desired compound as a yellow oily substance.

Workup

  1. waithydrogenation was continued for one hour
  2. customThe catalyst was removed
  3. filtrationby filtering the reaction solution through celite
  4. dry with materialthe filtrate was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7da79f04de9b404eb2c0cbf2e9cd2902
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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