Benzyl Bromide → 7-Benzyl-3-phenylxanthine

HRID 323862Notes

Reaction equation

HRID 323862 reaction equation
[OH-].[Na+].[C:3]1([N:9]2[C:17]3[N:16]=[CH:15][NH:14][C:13]=3[C:12](=[O:18])[NH:11][C:10]2=[O:19])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O.CO>[CH2:20]([N:14]1[C:13]2[C:12](=[O:18])[NH:11][C:10](=[O:19])[N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:17]=2[N:16]=[CH:15]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 1939375HCID 1939375, compound

Product 1

HCID 104957677-Benzyl-3-phenylxanthine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 0.53 g (13.2 mmol) of sodium hydroxide in 5.3 ml of water was added to a suspension of 3.0 g (13.2 mmol) of 3-phenylxanthine in 18 ml of methanol and the mixture was stirred at 70° C. for 1 hour. It was then treated dropwise with 1.56 ml (13.2 mmol) of benzyl bromide and stirred at 70° C. for 7 hours, the precipitate was filtered off with suction after cooling, washed with water and dissolved in 50 ml of 1 N sodium hydroxide solution, insoluble matter was filtered off and the solution was adjusted to pH 8-9 using 4 N hydrochloric acid. The resulting precipitate was filtered off with suction, washed with water and purified by flash chromatography on a silica gel column, dichloromethane/methanol (79/1).

Workup

  1. stirringstirred at 70° C. for 7 hours
  2. filtrationthe precipitate was filtered off with suction
  3. temperatureafter cooling
  4. washwashed with water
  5. dissolutiondissolved in 50 ml of 1 N sodium hydroxide solution
  6. filtrationinsoluble matter was filtered off
  7. filtrationThe resulting precipitate was filtered off with suction
  8. washwashed with water
  9. custompurified by flash chromatography on a silica gel column, dichloromethane/methanol (79/1)

Sources & evidence

ORD record
ord-e13ee313013541aeb20b51b270b6fcda
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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