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

HRID 524481Notes

Reaction equation

HRID 524481 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-d7b61ac1271348f4957fc431cc72a02d
Source dataset
uspto-grants-2016_05
Patent number
US09340544B2

Reaction notes

Loading…