Bromine → HCID 12016647, compound

HRID 377583Notes

Reaction equation

HRID 377583 reaction equation
[Br:1]Br.[CH2:3]([N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([CH3:20])=[N:14][C:15]=2[NH2:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CC([O-])=O.[Na+]>CC(O)=O>[CH2:3]([N:10]1[C:18]([Br:1])=[N:17][C:16]2[C:11]1=[N:12][C:13]([CH3:20])=[N:14][C:15]=2[NH2:19])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 15886851HCID 15886851, compound

Product 1

HCID 12016647HCID 12016647, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Bromine (0.2 ml) was added to a solution of 9-benzyl-2-methyladenine 60 mg (0.25 mmol) and NaOAc (0.22 g) in AcOH (5 ml), and the mixture was heated at 70° C. for 40 min. The solvent was evaporated under vacuum, and the residue was extracted by EtOAc. The resulting organic layer was evaporated under vacuum, and the residue was purified by column chromatography (CH2Cl2 :MeOH=50:1) to obtain 9-benzyl-8-bromo-2-methyladenine as an orange solid (60 mg). A mixture of the resulting 9-benzyl-8-bromo-2-methyladenine (60 mg) and conc.HCl (5 ml) was refluxed for 3 h. After cooling, aqueous NH3 was added to crystallize the product, and the desired compound was collected by filtration (10 mg, Yield: 16%).

Workup

  1. customThe solvent was evaporated under vacuum
  2. extractionthe residue was extracted by EtOAc
  3. customThe resulting organic layer was evaporated under vacuum
  4. customthe residue was purified by column chromatography (CH2Cl2 :MeOH=50:1)

Sources & evidence

ORD record
ord-13959b615fe24cd293cb637337be1149
Source dataset
uspto-grants-2000_02
Patent number
US06028076

Reaction notes

Loading…