4-CHLORO-1H-PYRAZOLO[3,4-D]PYRIMIDIN-6-AMINE Chemical Properties

Boiling point:

282.3±50.0 °C(Predicted)

Density 

2.09±0.1 g/cm3(Predicted)

storage temp. 

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

pka

9.35±0.20(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C5H4ClN5/c6-3-2-1-8-11-4(2)10-5(7)9-3/h1H,(H3,7,8,9,10,11)

InChIKey

ASKOHPBJRRSUSJ-UHFFFAOYSA-N

SMILES

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

Safety Information

RIDADR 

UN2811

HS Code 

2933599590

4-CHLORO-1H-PYRAZOLO[3,4-D]PYRIMIDIN-6-AMINE Usage And Synthesis

Uses

4-Chloro-1H-pyrazolo[3,4-D]pyrimidine-6-amine is a pyrimidine derivative that can be used as a pharmaceutical intermediate.

Synthesis

GENERAL STEPS: A mixture of 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (1.92 g, 10 mmol) and triethylamine (1.59 mL, 11.5 mmol) was added to a solvent mixture of THF (40 mL) and H2O (4 mL) at room temperature. Subsequently, hydrazine (64%, 486 μL, 10 mmol) was added slowly and dropwise. The reaction mixture was stirred continuously for 4 h at room temperature. Upon completion of the reaction, the volatiles were removed by distillation under reduced pressure. The residue was precipitated with water, and the resulting precipitate was washed with water and dried under vacuum to afford the target product 4-chloro-1H-pyrazolo[3,4-D]pyrimidin-6-amine (1.8 g, quantitatively) as a yellow solid.13C NMR (DMSO-d6, 75 MHz) δ: 161.5 (C-2), 157.5 (C-4), 153.2 (C-7a), 132.7 (C-5), 105.8 (C-4a).MS (m/z): 170 [M + H]+.

References

[1] Patent: WO2014/96423, 2014, A1. Location in patent: Page/Page column 50
[2] Patent: CN103804447, 2016, B. Location in patent: Paragraph 0076; 0082; 0083; 0084
[3] Synlett, 2011, # 13, p. 1900 - 1904
[4] Patent: WO2012/135084, 2012, A1. Location in patent: Page/Page column 17
[5] Patent: US2012/202785, 2012, A1. Location in patent: Page/Page column 262

4-CHLORO-1H-PYRAZOLO[3,4-D]PYRIMIDIN-6-AMINE(100644-65-3)Related Product Information

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