Potassium Carbonate → 6-Bromo-9-[(4-methoxyphenyl)methyl]purine

HRID 525006Notes

Reaction equation

HRID 525006 reaction equation
[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>CN(C=O)C>[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178419477HCID 178419477, compound

Product 1

HCID 596273846-Bromo-9-[(4-methoxyphenyl)methyl]purineYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.00 g (5.02 mmol) of 6-bromo-9H-purine (purchased from Aldrich; cat. no. 104981) was suspended in 10 mL of DMF and potassium carbonate (2.08 g, 15.05 mmol) was added. The mixture was stirred at room temperature for 20 minutes and then 1-(chloromethyl)-4-methoxybenzene (1.40 mL, 10.06 mmol) were added. The reaction mixture was stirred at 45° C. overnight. Then the mixture was evaporated to dryness and the residue was partitioned between water and dichloromethane. The organic layer was washed with water and brine, dried over magnesium sulphate, filtered and the solvent was removed in vacuum. The product was purified by flash chromatography (0% to 50% hexane/AcOEt) to yield 447 mg (28%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at 45° C. overnight
  2. customThen the mixture was evaporated to dryness
  3. customthe residue was partitioned between water and dichloromethane
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuum
  8. customThe product was purified by flash chromatography (0% to 50% hexane/AcOEt)

Sources & evidence

ORD record
ord-69563e657f71439cbee8fdb7473cc8e6
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

Loading…