Benzyl Bromide → 7-Benzyl-3-phenylxanthine

HRID 2052Notes

Reaction equation

HRID 2052 reaction equation
[H-].[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>CN(C=O)C>[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

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1939375HCID 1939375, compound

Product 1

HCID 104957677-Benzyl-3-phenylxanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

3.2 g (0.1315 mol) of sodium hydride were added in portions to a suspension of 30 g (0.1315 mol) of 3-phenylxanthine in 600 ml of DMF, the mixture was stirred at 25° C. for 30 minutes and then heated to 80° C. 27 g (0.1578 mol) of benzyl bromide were then added and the solution was left at 80° C. for 6 hours. After cooling to 50° C., the reaction mixture was poured into 2000 ml of ice-water, and the precipitate obtained was filtered off with suction, washed well with water and dried under reduced pressure. The dry residue was crystallized from dioxane/methanol.

Workup

  1. temperatureheated to 80° C
  2. waitthe solution was left at 80° C. for 6 hours
  3. temperatureAfter cooling to 50° C.
  4. customthe precipitate obtained
  5. filtrationwas filtered off with suction
  6. washwashed well with water
  7. customdried under reduced pressure
  8. customThe dry residue was crystallized from dioxane/methanol

Sources & evidence

ORD record
ord-5fefdaf5b899469aa937eb0977a556aa
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Reaction notes

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