Potassium Carbonate → HCID 22180671, compound

HRID 1795860Notes

Reaction equation

HRID 1795860 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[I-].[NH2:31][N+:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1>CN(C=O)C>[C:1]1([C:7]2[C:8]([C:9]3[CH:14]=[N:13][C:12]([S:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)(=[O:17])=[O:16])=[CH:11][CH:10]=3)=[C:33]3[CH:34]=[N:35][CH:36]=[CH:37][N:32]3[N:31]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate3×HCID 221806601-Aminopyrazin-1-ium iodide3×HCID 22180661HCID 22180661, compound

Product 1

HCID 22180671HCID 22180671, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-(phenylethynyl)-2-(phenylsulfonyl)pyridine (6.00 g) and K2CO3 (13.0 g) in DMF (120 mL) was added 1-aminopyrazin-1-ium iodide (12.6 g) and the mixture was stirred at room temperature for 1 h, then stirred at 60° C. for 8 h. To the reaction mixture was added K2CO3 (7.80 g) and 1-aminopyrazin-1-ium iodide (8.38 g) and stirred at room temperature for 1 h, then stirred at 60° C. for 12 h. To the reaction mixture was added further K2CO3 (7.80 g) and 1-aminopyrazin-1-ium iodide (8.38 g) and stirred at room temperature for 1 h, then stirred at 60° C. for 26 h. The mixture was poured into ice water and 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 3:1 to CHCl3-MeOH 20:1) to give 2-phenyl-3-[6-(phenylsulfonyl)-3-pyridinyl]pyrazolo[1,5-a]pyrazine (4.14 g) as an amorphous solid.

Workup

  1. stirringstirred at 60° C. for 8 h
  2. stirringstirred at room temperature for 1 h
  3. stirringstirred at 60° C. for 12 h
  4. stirringstirred at room temperature for 1 h
  5. stirringstirred at 60° C. for 26 h
  6. extractionextracted with EtOAc
  7. washwashed with water and brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography (n-hexane-EtOAc 3:1 to CHCl3-MeOH 20:1)

Sources & evidence

ORD record
ord-f7ce26d48007487f902b130deb9d7092
Source dataset
uspto-grants-2006_04
Patent number
US07030121B2

Reaction notes

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