Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 5,6-Diphenyl-2-(5-hydroxy-1-pentyn-1-yl)pyrazine

HRID 1271302Notes

Reaction equation

HRID 1271302 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][O:24]C3CCCCO3)=[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.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[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:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 229319555,6-Diphenyl-2-[5-(2-tetrahydropyranyloxy)-1-pentyn-1-yl]pyrazine

Product 1

HCID 229319465,6-Diphenyl-2-(5-hydroxy-1-pentyn-1-yl)pyrazineYield 70.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.79 g of 5,6-diphenyl-2-[5-(2-tetrahydropyranyloxy)-1-pentyn-1-yl]pyrazine in methanol, 1.13 g of pyridinium p-toluenesulfonate was added and the mixture was heated at reflux for 30 minutes. The reaction solution was poured into ice water while stirring, extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting crystal was recrystallized from diisopropyl ether to obtain 1.00 g of the desired compound as a yellow crystal having a melting point of 88 to 90° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe resulting crystal was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-fd04997f8c6f45868b02f0b8769f2275
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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