5,7-dichlorothiazolo[5,4-d]pyrimidine Chemical Properties

Melting point:

148.5-149.5 °C

Boiling point:

281.2±22.0 °C(Predicted)

Density 

1.767±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMF: 2 mg/ml,DMSO: 1 mg/ml,Ethanol: insol,PBS (pH 7.2): insol

form 

A solid

pka

-2.68±0.50(Predicted)

color 

Light yellow to brown

InChI

InChI=1S/C5HCl2N3S/c6-3-2-4(11-1-8-2)10-5(7)9-3/h1H

InChIKey

XYBGDWLYHQAUQM-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=C2N=CSC2=N1

5,7-dichlorothiazolo[5,4-d]pyrimidine Usage And Synthesis

Uses

5,7-Dichlorothiazolo[5,4-d]pyrimidine was used in studies to prepare Kinase inhibitors.

Synthesis

The general procedure for the synthesis of 5,7-dichlorothiazolo[5,4-d]pyrimidine using thiazolo[5,4-d]pyrimidine-5,7(4H,6H)-dione as starting material was as follows: a 10 mL round bottom flask was charged with intermediate 45.2 (100 mg, 0.59 mmol, 1.00 equiv.), N,N-diisopropylethylamine (DIEA, 0.5 mL) and phosphorus oxychloride (POCl3, 2 mL). The reaction mixture was stirred at 100 °C for 12 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography to afford intermediate 45.3 (100 mg, 82% yield) as a yellow oil.

References

[1] Heterocycles, 2012, vol. 85, # 7, p. 1721 - 1726
[2] Patent: WO2015/48281, 2015, A1. Location in patent: Paragraph 00472; 00475
[3] Patent: WO2014/15291, 2014, A1. Location in patent: Page/Page column 168; 169
[4] Journal of the American Chemical Society, 1951, vol. 73, p. 3862

5,7-dichlorothiazolo[5,4-d]pyrimidine(13479-88-4)Related Product Information

• 5,7-dichlorothiazolo[5,4-d]pyrimidine