Potassium peroxymonosulphate → 2-chloro-8-(methylsulfonyl)-7H-purine

HRID 929188Notes

Reaction equation

HRID 929188 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7](SC)=[N:8]2)=[CH:4][N:3]=1.[S:13]([O-:18])(O[O-])(=O)=[O:14].[K+].[K+].[CH3:21]C#N.O>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([S:13]([CH3:21])(=[O:18])=[O:14])=[N:8]2)=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 10313463Potassium peroxymonosulphateHCID 18373917Acetonitrile--water (1/1)HCID 457896422-Chloro-8-(methylsulfanyl)-7H-purine

Product 1

HCID 900418402-chloro-8-(methylsulfonyl)-7H-purine

Procedure

To a stirring solution of 2-chloro-8-(methylthio)-7H-purine (700.0 mg, 3.49 mmol) in 50% CH3CN/water (44.8 mL) was added potassium peroxymonosulfate (oxone, 4.72 g, 7.68 mmol). The reaction was stirred under N2 at RT for 17 h, then filtered and the filtrate was added to a stirring EtOAc (1 L)/water (0.56 L) mixture. The aqueous layer was separated and back-extracted with EtOAc (0.2 L). The combined organic layers were evaporated under reduced pressure to afford the title compound. LC-MS: calculated for C6H5ClN4O2S 231.98 observed m/e: 233.11 (M+H)+ (Rt 0.58/2.0 min).

Workup

  1. filtrationfiltered
  2. additionthe filtrate was added to a stirring EtOAc (1 L)/water (0.56 L) mixture
  3. customThe aqueous layer was separated
  4. extractionback-extracted with EtOAc (0.2 L)
  5. customThe combined organic layers were evaporated under reduced pressure

Sources & evidence

ORD record
ord-ad17307b7001478ba47827fc0ed4eb03
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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