4,5,6,7-TETRAHYDROPYRAZOLO[1,5-A]PYRIMIDINE Chemical Properties

Boiling point:

290℃

Density 

1.33

Flash point:

129℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.52±0.20(Predicted)

Appearance

Off-white to yellow Solid

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

4,5,6,7-TETRAHYDROPYRAZOLO[1,5-A]PYRIMIDINE Usage And Synthesis

Uses

4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine can be used as FGFR inhibitors to treat FGFR3-associated diseases, such as, cancer.

Synthesis

To a solution of 3H-pyrazol-3-amine (9.8 g, 0.1 mol) and triethylamine (TEA, 36.0 g, 0.3 mol) in 1,4-dioxane (200 mL) was added 1,3-dibromopropane (26.3 g, 0.1 mol). The reaction mixture was stirred at 110 °C for 5 hours. After the reaction was complete, the mixture was filtered. The filtrate was concentrated to dryness. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol = 100/1) to afford 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (5.3 g, yield: 36%) as a white solid.1H NMR (300 MHz, CDCl3): δ = 7.18 (s, 1H), 5.26 (s, 1H), 4.22-4.00 (m, 3H), 3.26-3.22 (m, 2H), 2.11-2.03 (m, 2H).

References

[1] Patent: WO2018/136890, 2018, A1. Location in patent: Paragraph 001018; 001019; 001020
[2] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 3, p. 557 - 567

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