5-bromo-4-chlorothieno[2,3-d]pyrimidine Chemical Properties

Boiling point:

345.5±37.0 °C(Predicted)

Density 

1.955±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-0.31±0.40(Predicted)

Appearance

White to yellow Solid

CAS DataBase Reference

814918-95-1

5-bromo-4-chlorothieno[2,3-d]pyrimidine Usage And Synthesis

Synthesis

To a solution of diisopropylamine (1.028 mL, 7.21 mmol, 1.8 eq.) dissolved in 10 mL of THF at 0 °C was slowly added n-butyllithium (3.76 mL, 6.01 mmol, 1.5 eq.). After 1 hr of reaction, the resulting LDA solution was transferred to a 35 mL THF solution containing 6-bromo-4-chlorothieno[2,3-d]pyrimidine (1.0 g, 4.01 mmol, 1.0 eq.) at -78 °C and under nitrogen protection. Stirring was continued at -78 °C for 1 h. A mixture consisting of 1.25 mL of water and 5 mL of THF was then slowly added. The reaction mixture was gradually warmed to 0 °C, poured into 60 mL of water and extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a yellow solid. The crude product was purified by silica gel column chromatography using a 20% ethyl acetate/hexane gradient elution to give 5-bromo-4-chlorothieno[2,3-d]pyrimidine (tan solid, 671 mg, 67.1% yield). NMR hydrogen spectrum (400 MHz, chloroform-d) δ 8.85 (s, 1H), 7.64 (s, 1H).

References

[1] Patent: WO2012/44993, 2012, A1. Location in patent: Page/Page column 44
[2] Patent: WO2017/46739, 2017, A1. Location in patent: Page/Page column 53
[3] Patent: US2006/89370, 2006, A1. Location in patent: Page/Page column 13-14
[4] Patent: WO2015/136463, 2015, A1. Location in patent: Page/Page column 137
[5] Patent: WO2004/111057, 2004, A1. Location in patent: Page 58-59

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