Hydrochloric Acid → 9-Benzylguanine

HRID 1588948Notes

Reaction equation

HRID 1588948 reaction equation
[CH2:1]([N:8]1[C:12]([NH:13][C:14](=S)[NH2:15])=[C:11]([C:17]([NH2:19])=[O:18])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.O.Cl>[OH-].[Na+].[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH2:1]([N:8]1[CH:9]=[N:10][C:11]2[C:17](=[O:18])[NH:19][C:14]([NH2:15])=[N:13][C:12]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 14897147HCID 14897147, compound

Product 1

HCID 1354161339-BenzylguanineYield 54%

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 14798Sodium HydroxideSolvent

Procedure

1-Benzyl-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide (2.75 g, 10.0 mM) and sodium tungstate (0.1 g) were suspended in 6N sodium hydroxide (20 ml) at 5° C. 35% hydrogen peroxide (4.0 ml, 44 mM) was added dropwise at 5°-15° C. over 30 minutes. Water (60 ml) was added to the resulting reaction mixture. After stirring for 1 hour in an ice bath pH was adjusted to 5 with hydrochloric acid. The formed product was filtered off, washed with water and dried. Hereby was isolated 1.30 g (54%) of the title compound as a white powder. HPLC indicated about 98% purity. The product had the same physical data as the product of example 4.

Workup

  1. filtrationThe formed product was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-83234d7a7a384d52aecd2c2d90b0ed66
Source dataset
uspto-grants-1993_06
Patent number
US05223619

Reaction notes

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