Water → 9-Methylguanine

HRID 1588945Notes

Reaction equation

HRID 1588945 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8](=S)[NH2:9])=[C:5]([C:11]([NH2:13])=[O:12])[N:4]=[CH:3]1.O>[OH-].[Na+].C([O-])(=O)C.[Cu+2].C([O-])(=O)C.[Cu]=S>[CH3:1][N:2]1[CH:3]=[N:4][C:5]2[C:11](=[O:12])[NH:13][C:8]([NH2:9])=[N:7][C:6]1=2

Participants

6

Reactant 2

HCID 962WaterHCID 148971451-Methyl-5-thioureido-1H-imidazole-4-carboxamide

Product 1

HCID 1354035919-MethylguanineYield 96%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 14831Copper monosulfideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

1-Methyl-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide (3.98 g, 20 mM) was dissolved in 1N sodium hydroxide (160 ml). Copper acetate, H2O (4.6 g, 23 mM) was added and the reaction mixture as then refluxed for 1 hour. After cooling to 50° C. the formed copper sulphide was filtered off. The filtrate was acidified with acetic acid to pH 5.0. The resulting product was filtered off at 25° C. washed with water and dried. Hereby was isolated 3.16 g (96%) of the title compound as a white powder, mp. >300° C. 13C-NMR(1N NaOD) δppm: 170.7; 163.6; 154.0, 141.4; 120.0; 32.2.

Workup

  1. temperaturethe reaction mixture as then refluxed for 1 hour
  2. filtrationwas filtered off
  3. filtrationThe resulting product was filtered off at 25° C.
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-67fdbeacb6f24fb49a13e16b9d835c34
Source dataset
uspto-grants-1993_06
Patent number
US05223619

Reaction notes

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