Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical Properties

Density 

1.47±0.1 g/cm3(Predicted)

storage temp. 

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

pka

-2.44±0.40(Predicted)

Appearance

white to brown solid

InChI

InChI=1S/C9H8ClN3O2/c1-2-15-9(14)6-5-11-13-4-3-7(10)12-8(6)13/h3-5H,2H2,1H3

InChIKey

UOZKVCQDLXBWBG-UHFFFAOYSA-N

SMILES

C12=C(C(OCC)=O)C=NN1C=CC(Cl)=N2

Safety Information

HS Code 

2933599590

Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate Usage And Synthesis

Uses

Ethyl 5-Chloropyrazolo[1,5-a]pyrimidine-3-carboxylate is used in preparation of antitumor pyrazolopyrimidine compound and it intermediates.

Synthesis

Step B: Preparation of ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate; Ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate (22.7 g, 110 mmol) was suspended in phosphorus triclosan (100 mL) and heated to reflux. After maintaining the reflux reaction for 2 h, the reaction mixture was cooled and the excess phosphorous trichloride was removed by distillation under reduced pressure. The residue was diluted with dichloromethane (100 mL) and slowly poured into a flask containing ice water. The organic and aqueous layers were separated and the aqueous layer was further extracted with dichloromethane. All organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (24.2 g, 97.6% yield) as a light yellow solid. Mass spectrum (APCI) m/z = 225.9 (M + H).

References

[1] Patent: WO2011/6074, 2011, A1. Location in patent: Page/Page column 70-71
[2] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 11, p. 1058 - 1077
[3] Patent: WO2012/34095, 2012, A1. Location in patent: Page/Page column 68
[4] Patent: US2016/159808, 2016, A1. Location in patent: Paragraph 1357; 1358; 1381; 1382; 1394; 1395
[5] Patent: TW2016/520, 2016, A. Location in patent: Paragraph 0165

Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate(1224944-77-7)Related Product Information

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