Water → 2,6-dichloro-9-methyl-9H-purine

HRID 1809203Notes

Reaction equation

HRID 1809203 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([Cl:13])[N:5]=1.[CH3:14]I.O>O1CCCC1>[Cl:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH3:14])=[C:6]([Cl:13])[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53244122,6-Dichloropurine

Product 1

HCID 17125532,6-dichloro-9-methyl-9H-purineYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in mineral oil, 2.53 g, 63.5 mmol) was added to an ice-cooled solution of 2,6-dichloropurine (10.0 g, 52.9 mmol) in tetrahydrofuran (75 mL) and the mixture was stirred for 30 min. Methyl iodide (3.29 mL, 52.9 mmol) was added drop-wise and the reaction mixture was stirred over night. Water was added and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated in vacuo. Dichloromethane was added and undissolved material was collected by filtration. The crystalline compound turned out to be 2,6-dichloro-7-methyl-7H-purine (1.19 g, 11%) The filtrate was concentrated in vacuo and purified by flash chromatography (ethyl acetate/hepatane) to give 2,6-dichloro-9-methyl-9H-purine (3.0 g, 28%).

Workup

  1. stirringthe reaction mixture was stirred over night
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionDichloromethane was added
  7. filtrationundissolved material was collected by filtration
  8. concentrationwas concentrated in vacuo
  9. custompurified by flash chromatography (ethyl acetate/hepatane)

Sources & evidence

ORD record
ord-324111a5a44549eca308ac8d04b0801e
Source dataset
uspto-grants-2013_01
Patent number
US08362024B2

Reaction notes

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