Methyl iodide → 2-Chloro-8-(methylsulfanyl)-7H-purine

HRID 929187Notes

Reaction equation

HRID 929187 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7](=[S:11])[NH:8]2)=[CH:4][N:3]=1.[OH-].[K+].I[CH3:15]>CCO>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([S:11][CH3:15])=[N:8]2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 53553492-chloro-9H-purin-8-yl hydrosulfide

Product 1

HCID 457896422-Chloro-8-(methylsulfanyl)-7H-purine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 2-chloro-7H-purine-8(9H)-thione (2.00 g, 10.72 mmol) and potassium hydroxide (722 mg, 12.86 mmol) in anhydrous EtOH (66.4 mL) was added iodomethane (0.67 mL, 10.72 mmol). The reaction solution was stirred under N2 at RT for 4 h, then partitioned between EtOAc (85 mL) and 2N HCl (15 mL) and allowed to settle overnight. To the aqueous layer, which contained solid material, was added more water (60 mL). The mixture was filtered, and dried under vacuum to afford the title compound as a solid. LC-MS: calculated for C6H5ClN4S 199.99 observed m/e: 200.99 (M+H)+ (Rt 0.99/1.8 min).

Workup

  1. custompartitioned between EtOAc (85 mL) and 2N HCl (15 mL)
  2. waitto settle overnight
  3. additionwas added more water (60 mL)
  4. filtrationThe mixture was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-92a5680b5d224a09a31d85d0638c6cb9
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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