13223-43-3

Basic information

• Product Name: 2-Amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine
• Synonyms: 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine;5,7-DIMETHOXY-[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-2-AMINE;2-Amino-5,7-Dimethoxy-1,2,4-Triazole-[1,5-A]-Pyrimidine;2-Amino-5,7-Dimethoxy-1,2,4-Tr;[1,2,4]Triazolo[1,5-a]pyrimidin-2-amine,5,7-dimethoxy-
• CAS NO: 13223-43-3
• Molecular Formula: C₇H₉N₅O₂
• Molecular Weight: 195.18
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 13223-43-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 215-220 ℃
• Appearance: /
• Density: 1.61 g/cm³
• Refractive Index: 1.705
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.85±0.30(Predicted)
• CAS DataBase Reference: 2-Amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine(13223-43-3)
• EPA Substance Registry System: 2-Amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine(13223-43-3)

Safety Data

• Hazardous Substances Data: 13223-43-3(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C7H9N5O2/c1-13-4-3-5(14-2)12-7(9-4)10-6(8)11-12/h3H,1-2H3,(H2,8,11)

Upstream product

• 102739-44-6 1-(ethoxycarbonyl)-3-(4,6-dimethoxy-pyrimidine-2-yl)-thiourea 
• 13223-25-1 2-chloro-4,6-dimethoxypyrimidine 
• 36315-01-2 4,6-dimethoxy-2-aminopyrimidine 
• 16182-04-0 Ethoxycarbonyl isothiocyanate 

Downstream Products

• 422556-08-9 pyroxsulam 

Relevant articles and documents

Application of the tisler triazolopyrimidine cyclization to the synthesis of a crop protection agent and an intermediate

A new synthetic route to the Dow AgroSciences early stage sulfonamide herbicide 3-(2-methoxy-4-trifluoromethyl)-N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a] pyrimidin-2-yl)pyridinesulfonamide (pyroxsulam) has been developed. The synthesis is based on formation of the triazole ring as the final step, utilizing the Tisler triazolopyrimidine cyclization. A Tisler cyclization route to 2-amino-5,7-dimethoxy-1,2,4-trazolo[1,5-a]pyrimidine starting with 2-chloro-4,6-dimethoxypyrimidine has also been demonstrated.

Method for preparing 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine

The invention discloses a method for preparing 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine, and relates to the technical field of production and processing of 2,2-dimethyl-thiazolidine. The method includes the steps of first condensation; layering; second condensation; filtering; ring formation; filtering; drying. According to the method for preparing 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine, after potassium thiocyanate is dropwise added into ethyl chloroformate and thorough reacting is achieved, generated potassium chloride is removed, 2-amino-4,6-dimethoxy pyrimidine is added into filtered liquid, condensation reaction, filtering, loop formation, filtering and drying are carried out, and 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine is generated; the technology has the advantages that raw materials are easy to get, operation is easy, the number of side reactions is small, and product efficiency is high.

PROCESS FOR THE PREPARATION OF TRIAZOLOPYRIMIDINES

Process for the preparation of unsubstituted or substituted 2-amino-[1,2,4]triazolopyrimidines which comprises combining A) 2-amino-pyrimidine or its derivatives with alkyloxycarbonyl isothiocyanate or aryloxycarbonyl isothiocyanate with B) hydroxyl ammonium salt and a base wherein the reaction is carried out in a polar aprotic organic solvent in the temperature range of from 40 to 150 °C.