Hydrochloric Acid → 7-(4-Methoxybenzyl)guanine dihydrochloride

HRID 355532Notes

Reaction equation

HRID 355532 reaction equation
[C@@H]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)O[C@H](CO)[C@@H](O)[C@H]1O.[I-].[Na+].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][Cl:30])=[CH:27][CH:26]=1.[ClH:33]>CS(C)=O.CO>[ClH:30].[ClH:33].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:12]2[C:13]3[C:14](=[O:15])[NH:16][C:17]([NH2:18])=[N:19][C:20]=3[N:10]=[CH:11]2)=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 699934-Methyloxybenzyl chlorideHCID 135398635Guanosine

Product 1

HCID 1358451447-(4-Methoxybenzyl)guanine dihydrochlorideYield 34.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

Guanosine (5.7 g; 20.0 mmol) was dissolved in 13.2 ml of dimethylsulfoxide. To this solution were added sodium iodide (0.6 g; 4 mmol) and 4-methoxybenzyl chloride (6.8 ml; 50.2 mmol), and the mixture was stirred at room temperature for 19 h. Conc. hydrochloric acid (10 ml) was added thereto, and stirred at 45° C. for 1 h. The mixture was cooled down to room temperature. Methanol (50 ml) was added thereto, and the mixture was stirred at room temperature for 3 h. The crystals precipitated were filtered, washed well with methanol (20 ml×3), and then dried at 50° C. under reduced pressure to obtain 2.5 g of 7-(4-methoxybenzyl)guanine dihydrochloride (34.8%).

Workup

  1. stirringstirred at 45° C. for 1 h
  2. temperatureThe mixture was cooled down to room temperature
  3. stirringthe mixture was stirred at room temperature for 3 h
  4. customThe crystals precipitated
  5. filtrationwere filtered
  6. washwashed well with methanol (20 ml×3)
  7. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-b6b2cfb4e61a4f34b5df3d71d47fd11b
Source dataset
uspto-grants-1998_11
Patent number
US05831092

Reaction notes

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