Tetrahydrofuran → HCID 53386373, compound

HRID 2370069Notes

Reaction equation

HRID 2370069 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:25][CH2:26]SC)[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)[N:13]=[C:12]([CH3:24])[N:11]=2.[S:29]([O-:34])(O[O-])(=O)=[O:30].[K+].[K+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].O1CCC[CH2:47]1>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:25][CH2:26][S:29]([CH3:47])(=[O:34])=[O:30])[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)[N:13]=[C:12]([CH3:24])[N:11]=2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 656671Sodium PyrosulfiteHCID 10313463Potassium peroxymonosulphate3×HCID 67447519HCID 67447519, compound

Product 1

HCID 53386373HCID 53386373, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve 8-(2-chlorophenyl)-2-methyl-6-(4-methylpiperazin-1-yl)-9-(2-methylsulfanylethyl)purine (38.5 g, 92.3 mmol) in a solution of tetrahydrofuran (277 mL) and methanol (277 mL). Prepare a solution of potassium peroxymonosulfate (Oxone®) (79.5 g, 129.3 mmol) in water (554 mL). Add the potassium peroxymonosulfate solution (300 mL) over a 5 min period and stir for 30 min. Then add additional potassium peroxymonosulfate solution (150 mL, followed by 50 mL after 30 min). Stir the reaction mixture for 30 min following the final addition. Add solid sodium metabisulfite (49.1 g, 258.5 mmol) and stir the mixture at ambient temperature overnight. Add aqueous sodium bicarbonate solution (400 mL) and extract into ethyl acetate (3×1 L). Dry the combined organic layer over anhydrous sodium sulfate, filter, and concentrate to afford an orange residue. Purify the residue on a silica gel column using 5-50% ethanol in 1:1 dichloromethane-hexane as eluent. Combine and evaporate the appropriate fractions to provide a solid. Triturate the solid with ether and dry under vacuum to afford 8-(2-chlorophenyl)-2-methyl-6-(4-methylpiperazin-1-yl)-9-(2-methylsulfonylethyl)purine (11.4 g). ES/MS m/z 449 (M+1).

Workup

  1. stirringStir the reaction mixture for 30 min
  2. additionaddition
  3. stirringstir the mixture at ambient temperature overnight
  4. extractionAdd aqueous sodium bicarbonate solution (400 mL) and extract into ethyl acetate (3×1 L)
  5. dry with materialDry the combined organic layer over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto afford an orange residue
  9. customPurify the residue on a silica gel column
  10. customCombine and evaporate the appropriate fractions
  11. customto provide a solid
  12. customTriturate the solid with ether
  13. customdry under vacuum

Sources & evidence

ORD record
ord-059167c8d8c14895ae56616b60dde2da
Source dataset
uspto-grants-2014_04
Patent number
US08710063B2

Reaction notes

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