Methanol → HCID 67193251, compound

HRID 2401316Notes

Reaction equation

HRID 2401316 reaction equation
[CH:1]1([C:6]2[NH:14][C:13]3[C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH3:18])[C:10](Cl)=[N:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:22][OH:23]>>[CH:1]1([C:6]2[NH:14][C:13]3[C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH3:18])[C:10]([O:23][CH3:22])=[N:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 69937333HCID 69937333, compound

Product 1

HCID 67193251HCID 67193251, compoundYield 22%

Procedure

To a solution of 8-cyclopentyl-2-chloro-1-propyl-1,7-dihydro-purin-6-one (0.06 g, 0.21 mmol) in methanol (2 ml) was added NaH (60% dispersion in mineral oil, 0.085 g, 2.14 mmol) under nitrogen atmosphere and the reaction mixture was refluxed for 3 hours. After cooling to room temperature the reaction mixture was concentrated under reduced pressure. Water (10 ml) was added to the residue and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by preparative TLC using 2% methanol in dichloromethane as solvent system to give the product (0.013 g, 22%) as a white solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. concentrationwas concentrated under reduced pressure
  3. additionWater (10 ml) was added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-b0f4b697fbd54b439e096a6a3dbbfbd5
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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