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

HRID 1692861Notes

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-f6e82623cba244ebbb77e2a91b118806
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158625B2

Reaction notes

Loading…