7-CHLORO-5-METHYL-1,2,4-TRIAZOLE[1,5-A]PYRIMIDINE Chemical Properties

Melting point:

151-153 °C

Density 

1.59±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.03±0.30(Predicted)

Safety Information

HS Code 

2933998090

7-CHLORO-5-METHYL-1,2,4-TRIAZOLE[1,5-A]PYRIMIDINE Usage And Synthesis

Uses

7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine is a reactant used in the iron-catalyzed cross-coupling of organometallic compounds.

Synthesis

General procedure for the synthesis of 7-chloro-5-methyl-1,2,4-triazolo[1,5-α]pyrimidine from 7-hydroxy-5-methyl-1,3,4-tetraazaindolizine: to a solution of 7-hydroxy-5-methyl-1,3,4-tetraazaindolizine (1.60 g; 10.66 mmol) in dioxane (10 mL) was added sequentially phosphorous triclosulfate (2.5 mL; 26.65 mmol) and triethylamine (2.97 mL; 21.32 mmol). The reaction mixture was heated at 105 °C with stirring for 3 h. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted slowly and dropwise by adding sodium bicarbonate solution to 8. Subsequently, dichloromethane (DCM) was added for phase separation. The aqueous phase was further extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate and filtered. The solvent was removed by concentration under reduced pressure to give the crude product as an oil. The crude product was purified by column chromatography using a gradient elution from pure petroleum ether to 50% ethyl acetate/petroleum ether to afford 7-chloro-5-methyl-1,2,4-triazolo[1,5-alpha]pyrimidine (Compound 4) as a yellow solid (1.16 g, 65% yield).

References

[1] Tetrahedron Letters, 2018, vol. 59, # 11, p. 1050 - 1054
[2] Patent: WO2007/149211, 2007, A1. Location in patent: Page/Page column 23-24
[3] Monatshefte fuer Chemie, 1987, vol. 118, p. 601 - 606
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 7, p. 1864 - 1872
[5] European Journal of Medicinal Chemistry, 2016, vol. 119, p. 260 - 277

7-CHLORO-5-METHYL-1,2,4-TRIAZOLE[1,5-A]PYRIMIDINE(24415-66-5)Related Product Information

• 7-CHLORO-6-(2-CHLOROETHYL)-5-METHYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE
• methyl 7-chloro-5-ethyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate
• BUTTPARK 56\40-46
• methyl 7-chloro-5-isopropyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate
• 7-CHLORO-5-METHYL-1,2,4-TRIAZOLE[1,5-A]PYRIMIDINE
• methyl 7-chloro-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate
• methyl 5-tert-butyl-7-chloro[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate
• 7-CHLORO-5-METHYL-2-(TRIFLUOROMETHYL)[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE
• 7-chloro-5-pyridin-3-yl[1,2,4]triazolo[1,5-a]pyrimidine
• 7-chloro-5-isopropyl[1,2,4]triazolo[1,5-a]pyrimidine
• 5-tert-butyl-7-chloro[1,2,4]triazolo[1,5-a]pyrimidine
• 7-chloro-5-ethyl[1,2,4]triazolo[1,5-a]pyrimidine
• 7-chloro-5-propyl[1,2,4]triazolo[1,5-a]pyrimidine
• 7-chloro-5-phenyl[1,2,4]triazolo[1,5-a]pyrimidine
• 7-chloro-5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine