Water → HCID 18999869, compound

HRID 2260113Notes

Reaction equation

HRID 2260113 reaction equation
[H-].[Na+].[Cl:3][C:4]1[S:8][C:7]([C:9]2[CH:10]=[N:11][C:12]3[CH:13]=[C:14]4[CH:21]=[N:20][NH:19][C:15]4=[CH:16][C:17]=3[N:18]=2)=[CH:6][CH:5]=1.I[CH3:23].O>C1COCC1>[CH3:23][N:19]1[C:15]2=[CH:16][C:17]3[N:18]=[C:9]([C:7]4[S:8][C:4]([Cl:3])=[CH:5][CH:6]=4)[CH:10]=[N:11][C:12]=3[CH:13]=[C:14]2[CH:21]=[N:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15814132HCID 15814132, compound

Product 1

HCID 18999869HCID 18999869, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-colded suspension of NaH (0.062 g) in 20 ml of anhydrous THF under N2 is added 7-(5-chlorothien-2-yl)-1H-pyrazolo[3,4-g]quinoxaline (0.63 g). The orange-red mixture is stirred at the same temperature for 5 minutes, then iodomethane (0.374 g) is added dropwise to the orange-red mixture. The resulting mixture is stirred at room temperature overnight, then poured into water, extracted with methylene chloride, separated, dried (MeSO4), concentrated in vacuo to give a yellow solid. Purification is by chromatography eluting first with 5% ethylacetate in hexane, then gradually up to 30% ethylacetate in hexane to isolate 1-methyl-7-(5-chlorothien-2-yl)-1H-pyrazolo[3,4-g]quinoxaline (m.p. 225°-227° C.), then up to 10% hexane in ethylacetate to isolate 2-methyl-7-(5-chlorothien-2-yl)-2H-pyrazolo[3,4-g]quinoxaline (m.p. 222°-224° C.).

Workup

  1. stirringThe resulting mixture is stirred at room temperature overnight
  2. extractionextracted with methylene chloride
  3. customseparated
  4. dry with materialdried (MeSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid
  7. customPurification
  8. washeluting first with 5% ethylacetate in hexane

Sources & evidence

ORD record
ord-36dd87bb1e064b9aa788eb6dd6d23fa3
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Reaction notes

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