7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine Chemical Properties

Boiling point:

384.3±37.0 °C(Predicted)

Density 

1.996±0.06 g/cm3(Predicted)

storage temp. 

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

pka

9.91±0.40(Predicted)

Appearance

Light brown to brown Solid

Safety Information

HazardClass 

IRRITANT

7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine Usage And Synthesis

Synthesis

Under argon protection, 7-bromo-1,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one (100 mg, 0.5 mmol) was mixed with 6 mL of phosphorus oxytrichloride (POCl3) and the reaction was heated for 3 hours at 115 °C. After the reaction was completed, the mixture was cooled to room temperature and slowly poured into 300 mL of ice water with thorough stirring. The pH was adjusted to alkaline with potassium carbonate solution and subsequently extracted with ethyl acetate (EtOAc). The organic phases were combined, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to afford 101 mg (93% yield) of the target product, 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine, as a beige solid, which could be used in the subsequent reaction without further purification.

References

[1] Patent: WO2008/70507, 2008, A2. Location in patent: Page/Page column 153
[2] Patent: WO2015/128334, 2015, A1. Location in patent: Page/Page column 90
[3] Patent: WO2011/113798, 2011, A2. Location in patent: Page/Page column 59-60
[4] Patent: US2013/102587, 2013, A1. Location in patent: Paragraph 0273; 0274

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