5434-62-8

Usage

InChI:InChI=1/C13H12ClN5O2/c1-18-10-9(11(20)19(2)13(18)21)16-12(17-10)15-8-5-3-7(14)4-6-8/h3-6H,1-2H3,(H2,15,16,17)

Upstream product

• 77012-46-5 chlorure d'amino-4 (chloromethine N-dimethyl iminium)-5 dimethyl-1,3 uracile 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 

Relevant academic research and scientific papers

A new entry to the imidazo[4,5-d]pyrimidine system. The reaction of 1,3-dimethyl-6-aminouracil with N,N-dimethyldichloromethyleniminium chloride (phosgeniminium chloride) and trimethylsilyl azide

1,3-Dimethyl-6-aminouracil 2 was converted into various 8-N-arylaminotheophyllines (2-N-arylamino-4,6-dimethylimidazo[4,5-d]pyrimidine-(4H,6H)-5,7-diones ) 17 through reaction successively, with phosgeniminium chloride (N,N-dimethyldichloromethyleniminium chloride) (1a), trimethylsilyl azide (4) and arylamines. Starting with the synthesis of the N,N-dimethyl-(1,3-dimethyl-4-aminouracil-5 yl)chloromethyleniminiun chloride (amide chloride) 3 this new route to the imidazo[4,5-d]pyrimidine skeleton was shown to proceed via the formation of a very unstable N,N-dimethyl-(1,3-dimethyl-4-aminouracil-5-yl)azidomethyleniminium chloride (amide azide) (8) which would undergo an in situ rearrangement into very likely, a 4-amino-5-(chloroformamidin-1'-yl)uracil and/or related compounds of types 10. Depending on reaction conditions, the latter was proved to be a very good precursor of the 8-dimethylaminotheophylline 11 as well.