4-Chloro-1H-pyrazolo[3,4-d]pyrimidine Chemical Properties

Melting point:

>350?C

Boiling point:

224.6±50.0 °C(Predicted)

Density 

1.84±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

10.16±0.20(Predicted)

color 

Yellow to Orange

CAS DataBase Reference

5399-92-8(CAS DataBase Reference)

Safety Information

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

29335990

4-Chloro-1H-pyrazolo[3,4-d]pyrimidine Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

Has a SK channel blocker effect.

Synthesis

Synthesis of compound 4.1. Hydrazine hydrate (11.5 mL, 23.7 mmol) was slowly added dropwise to a 1,4-dioxane solution (600 mL) containing 4,6-dichloro-5-pyrimidinecarboxaldehyde (40.0 g, 22.6 mmol) and triethylamine (30 mL, 22 mmol) under the cooling of an ice bath, and the temperature of the reaction was controlled to be no more than 20°C. The reaction temperature was controlled to be no higher than 20°C. After dropwise addition, the reaction mixture was gradually warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the precipitate was collected by filtration. The filtrate was concentrated under reduced pressure to give compound 4.1 (29 g, 83% yield) in the form of a light yellow solid. The product was characterized by 1H NMR (400.13 MHz, DMSO-d6) and mass spectrometry: 1H NMR δ 14.52 (br.s, 1H), 8.83 (s, 1H), 8.45 (s, 1H); MS m/z 155 [M + 1]+.

References

[1] Patent: US2009/5359, 2009, A1. Location in patent: Page/Page column 18
[2] Patent: WO2008/153947, 2008, A2. Location in patent: Page/Page column 42; 63-64
[3] Molecules, 2017, vol. 22, # 4,
[4] Patent: CN106496232, 2017, A. Location in patent: Paragraph 0049; 0050; 0051; 0052
[5] Patent: CN107383014, 2017, A. Location in patent: Paragraph 0075; 0076; 0077; 0078

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