3-BROMO-4-CHLORO-1H-PYRAZOLO[3,4-D]PYRIMIDINE Chemical Properties

Boiling point:

270.3±50.0 °C(Predicted)

Density 

2.41±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

8.36±0.20(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C5H2BrClN4/c6-3-2-4(7)8-1-9-5(2)11-10-3/h1H,(H,8,9,10,11)

InChIKey

MDFHFCAMBZNSLV-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C2C(Br)=NNC2=N1

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

2933199090

3-BROMO-4-CHLORO-1H-PYRAZOLO[3,4-D]PYRIMIDINE Usage And Synthesis

Synthesis

4-Chloro-1H-pyrazolo[3,4-d]pyrimidine (1.1 g, 7.1 mmol) was used as starting material and suspended in CHCl3 (50 mL). N-bromosuccinimide (NBS, 1.49 g, 8.4 mmol) was added to the suspension under stirring. The reaction mixture was stirred at room temperature for 5 h and subsequently cooled to 0°C. The resulting solid product was separated by vacuum filtration and washed with cold CHCl3. The solid product was dried over air and further purified by silica gel column chromatography (eluent: 50% EtOAc/hexanes) to afford finally 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (1.3 g, 77% yield).

References

[1] Organic Letters, 2003, vol. 5, # 20, p. 3587 - 3590
[2] Patent: WO2005/51304, 2005, A2. Location in patent: Page/Page column 115-116
[3] Patent: WO2005/51304, 2005, A2. Location in patent: Page/Page column 115-116
[4] MedChemComm, 2018, vol. 9, # 8, p. 1340 - 1350
[5] Patent: WO2016/187723, 2016, A1. Location in patent: Page/Page column 51

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