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

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

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

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.

Synthesis, crystal structure and herbicidal activity of a series of [1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide compounds

With the aim of obtaining efficient, safe and environmentally friendly green herbicide, a series of [1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide compounds (8a-8f) were synthesized by reacting 2-amino-5,7-(bis-substituted)- 1,2,4-triazolo[1,5-a]pyrimidine (4a and 4b) with 2-substituted-6-trifluoromethyl-benzenesulfonyl chloride (7a-7c). And their structures were characterized by H-NMR, C-NMR, HRMS, FTIR, single-crystal X-ray diffraction, elemental analysis. Moreover, their herbicidal activities against six species of weeds were evaluated. Three target compounds such as 8a, 8c and 8e, exhibited significant postemergence herbicidal activity against some common dicotyledons and monocotyledons under different concentrations. The structure and activity relationship is discussed based on the herbicidal performances of the compounds with different substituents. The investigation results indicated that the above structures could serve as lead compounds for the development of new herbicides.

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.

Triazolopyrimidinylsulfonamide compound, composition containing compound, and application of compound

The invention discloses a triazolopyrimidinylsulfonamide compound having a structural formula shown in the description, a composition containing the compound, and an application of the compound. X1, X2, B1, B2, R1, R2, R3, R4 and R5 in the formula are as defined in the description. The triazolopyrimidinylsulfonamide compound has high growth inhibition activity on multiple broadleaf weeds and grassy weeds, has no obvious drug effects on corn, rice, cotton, wheat and other crops, also has the advantages of good crop safety, few synthesis steps, simple method and low preparation cost, and is suitable for large-scale industrial production.

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.

N- (5, 7-dimethoxy [1, 2, 4] triazolo [1, 5-a] pyrimidin-2-yl) arylsulfonamide compounds and their use as herbicides

N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl) arylsulfonamide compounds were prepared from 2-amino-5,7-dimethoxy[1,2,4]triazolopyrimidine and appropriately substituted benzenesulfonyl chloride and pyridinesulfonyl chloride compounds. The compounds were found to be useful as herbicides.

N-([1,2,4] triazoloazinyl) thiophenesulfonamide compounds and their use as herbicides

N-(Triazoloazinyl)thiophenesulfonamide compounds were prepared from appropriately substituted 2-amino[1,2,4]triazolo[1,5-c]pyrimidine, 2-amino[1,2,4]triazolo[1,5-a]pyrimidine and 2-amino[1,2,4]triazolo[1,5-a]pyridine compounds and appropriately substituted thiophenesulfonyl chloride compounds. The compounds were found to be useful as herbicides.