Sulfuric Acid → 5-Amino-1-methyl-1H-imidazole-4-carboxamide

HRID 1945624Notes

Reaction equation

[NH2:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[C:8]#[N:9].S(=O)(=O)(O)[OH:11]>>[NH2:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[C:8]([NH2:9])=[O:11]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 110516355-amino-1-methyl-1H-imidazole-4-carbonitrile

Product 1

HCID 64202875-Amino-1-methyl-1H-imidazole-4-carboxamide

Procedure

The cyano group of 5-amino-1-methyl-1H-imidazole-4-carbonitrile 1 is hydrolyzed with sulfuric acid to give 5-amino-1-methyl-1H-imidazole-4-carboxamide 2. Cyclization with urea gives 9-methyl-1H-purine-2,6(3H,9H)-dione 3. Chlorination with phosphorus pentachloride and phosphorusoxychloride gives 2,6-dichloro-9-methyl-9H-purine 4 (CAS Registry 2382-10-7).

Sources & evidence

ORD record: ord-126fd7c66f5042629f2856559f9ff7f8
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394796B2

Reaction notes

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