1H-Pyrazolo[4,3-d]pyriMidine, 5-chloro- Chemical Properties

Density 

1.653±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

6.68±0.50(Predicted)

form 

solid

color 

Yellow

InChI

InChI=1S/C5H3ClN4/c6-5-7-1-4-3(9-5)2-8-10-4/h1-2H,(H,8,10)

InChIKey

MRTKTXTWOUDUTL-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C2NN=CC2=N1

Safety Information

HS Code 

2933599590

1H-Pyrazolo[4,3-d]pyriMidine, 5-chloro- Usage And Synthesis

Uses

5-Chloro-1H-pyrazolo[4,3-D]pyrimidine is used in preparation of pyrimidine derivatives and related heterocycles as DNA-dependent protein kinase inhibitors for treatment of diseases.

Synthesis

General procedure for the synthesis of 5-chloro-1H-pyrazolo[4,3-d]pyrimidin-1-yl from 1-(5-chloro-1H-pyrazolo[4,3-d]pyrimidin-1-yl)ethanone: To a stirred solution of 1-(5-chloro-1H-pyrazolo[4,3-d]pyrimidin-1-yl)ethanone (1.5 g, 7.65 mmol) in tetrahydrofuran (THF, 15 mL), was added an 8% hydrochloric acid aqueous solution (14.46 mL). The reaction mixture was refluxed at 50 °C for 30 min. After completion of the reaction, it was cooled to 25 °C and extracted with ethyl acetate (EtOAc, 2 × 50 mL). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford 5-chloro-1H-pyrazolo[4,3-d]pyrimidine as an off-white solid (1.1 g, 93% yield). Mass spectrum (ESI): m/z = 153.0 [M-H]-.

References

[1] Patent: WO2017/137334, 2017, A1. Location in patent: Page/Page column 123; 124
[2] Patent: CN105906621, 2016, A. Location in patent: Paragraph 0035
[3] Patent: US2012/202785, 2012, A1. Location in patent: Page/Page column 263