4-Chlorothieno[3,2-d]pyrimidine Chemical Properties

Melting point:

125 °C

Boiling point:

285.7±20.0 °C(Predicted)

Density 

1.531±0.06 g/cm3(Predicted)

storage temp. 

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

form 

crystalline powder

pka

0.54±0.40(Predicted)

color 

Yellow

CAS DataBase Reference

16269-66-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn,T

Risk Statements 

22-36/37/38-36-25

Safety Statements 

26-37/39-45

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

29335990

4-Chlorothieno[3,2-d]pyrimidine Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-chlorothieno[3,2-d]pyrimidine using thieno[3,2-d]pyrimidin-4(3H)-one as starting material was as follows: dimethylformamide (15.4 mL, 197.13 mmol) was added to 150 mL of dichloroethane and the reaction system was cooled down to 0 °C. Subsequently, oxalyl chloride (25 mL, 295.70 mmol) was added slowly and dropwise. After the formation of a white gel-like substance was observed, 3H-thieno[3,2-d]pyrimidin-4-one (15 g, 98.57 mmol) was added. The reaction mixture was stirred at 0 °C for 2.5 h and then gradually warmed up to room temperature. Upon completion of the reaction, the reaction was quenched by the addition of water and the organic layer was extracted with dichloromethane (3 x 300 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure and the residue was ground with 200 mL of hexane to afford 4-chlorothieno[3,2-d]pyrimidine (16.7 g, 99% yield) as a dark brown solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 9.06 (s, 1H), 8.61 (d, J = 5.2 Hz, 1H), 7.78 (d, J = 5.2 Hz, 1H); LC-MS showed the molecular ion peak m/z 173.2 ([MH]+).

References

[1] Patent: US2013/72482, 2013, A1. Location in patent: Paragraph 0211; 0216; 0217
[2] Patent: WO2005/51304, 2005, A2. Location in patent: Page/Page column 67-68
[3] Patent: WO2005/51304, 2005, A2. Location in patent: Page/Page column 67-68
[4] Patent: WO2006/10264, 2006, A1. Location in patent: Page/Page column 51; 67-68
[5] MedChemComm, 2015, vol. 6, # 2, p. 339 - 346

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