Sodium Methoxide → HCID 9922442, compound

HRID 1795861Notes

Reaction equation

HRID 1795861 reaction equation
[C:1]1([C:7]2[C:15]([C:16]3[CH:17]=[N:18][C:19](S(C4C=CC=CC=4)(=O)=O)=[CH:20][CH:21]=3)=[C:10]3[CH:11]=[N:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:31][O-:32].[Na+]>CO.O1CCOCC1>[CH3:31][O:32][C:19]1[N:18]=[CH:17][C:16]([C:15]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:8][N:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=23)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 22180671HCID 22180671, compound

Product 1

HCID 9922442HCID 9922442, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-phenyl-3-[6-(phenylsulfonyl)-3-pyridinyl]pyrazolo[1,5-a]pyrazine (3.93 g) and sodium methoxide (5.2M MeOH solution, 10 mL) in MeOH (60 mL) and 1,4-dioxane (60 mL) was stirred at 85° C. for 1 h. The reaction mixture was concentrated in vacuo, and ice water was added, extracted, with EtOAc, washed with water and brine, dried over sodium sulfate, evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane-EtOAc 2:3) to give 3-(6-methoxy-3-pyridinyl)-2-phenylpyrazolo[1,5-a]pyrazine (2.37 g) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, and ice water
  2. additionwas added
  3. extractionextracted, with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (n-hexane-EtOAc 2:3)

Sources & evidence

ORD record
ord-759b6e827389444880d8138bcfaff4bd
Source dataset
uspto-grants-2006_04
Patent number
US07030121B2

Reaction notes

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