Benzyl Bromide → 7-benzyl-3,7-dihydro-6h-purin-6-one

HRID 501388Notes

Reaction equation

HRID 501388 reaction equation
[C@@H]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([OH:15])[C:13]=3[N:12]=[CH:11]2)O[C@H](CO)[C@@H](O)[C@H]1O.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OCC)(=O)C>CS(C)=O>[CH2:20]([N:12]1[C:13]2[C:14](=[O:15])[NH:16][CH:17]=[N:18][C:19]=2[N:10]=[CH:11]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Product 1

HCID 1354526937-benzyl-3,7-dihydro-6h-purin-6-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

18.23 g of inosine was dissolved in 90 ml of dimethyl sulfoxide, and 16 ml of benzyl bromide was added thereto. The mixture was stirred at room temperature overnight. The reaction solution was poured into 3 L of ethyl acetate. The resulting supernatant was removed and the precipitated oil was dissolved in 10% hydrochloric acid (135 ml). The solution was heated at 70° C. with stirring for 4 hours. The solution was cooled to room temperature, and then neutralized to pH 7 using a 5N aqueous sodium hydroxide solution. The precipitated solid was collected by filtration, and dried to give 12.748 g of the title compound.

Workup

  1. customThe resulting supernatant was removed
  2. dissolutionthe precipitated oil was dissolved in 10% hydrochloric acid (135 ml)
  3. temperatureThe solution was heated at 70° C.
  4. stirringwith stirring for 4 hours
  5. temperatureThe solution was cooled to room temperature
  6. filtrationThe precipitated solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-c7ae9daf44f648b192c4740730bd945a
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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