216085-09-5

Basic information

• Product Name: 1,2,4-Triazolo[4,3-a]pyrimidine-6-carbonitrile, 7,8-dihydro-8-methyl-7-oxo-3,5-diphenyl-
• CAS NO: 216085-09-5
• Molecular Formula: C19H13N5O
• Molecular Weight: 327.345
• Mol File: 216085-09-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2,4-Triazolo[4,3-a]pyrimidine-6-carbonitrile, 7,8-dihydro-8-methyl-7-oxo-3,5-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Triazolo[4,3-a]pyrimidine-6-carbonitrile, 7,8-dihydro-8-methyl-7-oxo-3,5-diphenyl-(216085-09-5)
• EPA Substance Registry System: 1,2,4-Triazolo[4,3-a]pyrimidine-6-carbonitrile, 7,8-dihydro-8-methyl-7-oxo-3,5-diphenyl-(216085-09-5)

Safety Data

• Hazardous Substances Data: 216085-09-5(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 97693-26-0 2-hydrazino-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile 
• 97693-31-7 Benzaldehyde (5-cyano-3-methyl-4-oxo-6-phenyl-3,4-dihydropyrimidin-2-yl)hydrazone 

Relevant articles and documents

Synthesis and Dimroth rearrangement of 6-cyano-1,2,4-triazolo-[4,3-a]pyrimidin-5- and 7-ones. A novel alkylation with orthoesters and a new participation of the cyano group in the rearrangement

The cyclization products of 5-cyano-2-hydrazino-6-phenyl-3,4-dihydropyrimidin-4-one (6) with one carbon inserting agents have been confirmed to be of the 1,2,4-triazolo[4,3-a]pyrimidin-5(8H)-ones type and not the respective 7-ones, by comparing their alkylated derivatives 10a, 11a, 27 and 28 with the product from the cyclization of the 3-methyl and 3-benzyl derivatives of 6. A novel alkylation process was found when triethyl orthoformate was used as a cyclizing agent. Dimroth rearrangement of 8, 14, 15, 24, 34 and 36 with 2% ethanolic KOH gave the respective triazolo[1,5-a]pyrimidinone 13, 18, 19, 25, 38 and 40, respectively. Using 10% ethanolic KOH led to a novel participation of the cyano group in the rearrangement whereby 8a gave 7-imino-5-phenyl-1,2,4-triazolo[1,5-a]pyrimidine 22.