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

Boiling point:

345.5±37.0 °C(Predicted)

Density 

1.955

storage temp. 

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

form 

solid

pka

-0.19±0.40(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C6H2BrClN2S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H

InChIKey

RJKAKJGOZXERRE-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C2SC(Br)=CC2=N1

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

HazardClass 

IRRITANT

HS Code 

2934999090

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

Synthesis

General procedure for the synthesis of 6-bromo-4-chlorothieno[3,2-d]pyrimidines from 4-chlorothieno[3,2-d]pyrimidines: to dry 200 mL of tetrahydrofuran was added lithium diisopropylamine (25 mL, 61.54 mmol), and the reaction system was cooled to -78 °C. Subsequently, 4-chlorothieno[3,2-d] Pyrimidine (5 g, 39.30 mmol) was slowly added dropwise to the above mixture. After 20 min of reaction, 1,2-dibromo-1,1,2,2-tetrafluoroethane (11.45 g, 35.17 mmol) was slowly added. Stirring was continued at -78°C for 20 minutes, then gradually warmed to room temperature and continued for 2 hours. Upon completion of the reaction, water was added to the mixture and extracted with chloroform (3 x 300 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the mixture was developed with 200 mL of hexane to afford 6-bromo-4-chlorothieno[3,2-d]pyrimidine (6.5 g, 89.2% yield) as a dark brown solid. The product was characterized by 1H-NMR (400 MHz, CDCl3): δ 8.94 (s, 1H), 7.62 (s, 1H); LC-MS showed molecular ion peaks of 249 and 251 (MH+).

References

[1] MedChemComm, 2015, vol. 6, # 2, p. 339 - 346
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[3] Patent: US2013/72482, 2013, A1. Location in patent: Paragraph 0211; 0218; 0219
[4] Patent: US2007/99941, 2007, A1. Location in patent: Page/Page column 15
[5] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 21 - 24

6-bromo-4-chlorothieno[3,2-d]pyrimidine(225385-03-5)Related Product Information

• 2-BROMO-3-THIOPHENECARBOXYLIC ACID 97
• 3-Bromothiophene
• Dibenzothiophene
• Dibromothiophene
• 4-Chlorothieno[3,2-d]pyrimidine
• 6-bromo-4-chlorothieno[3,2-d]pyrimidine