4-CHLOROTHIENO[2,3-D]PYRIMIDINE Chemical Properties

Melting point:

109-113°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

solubility 

Dichloromethane, DMSO

form 

Solid

pka

0.42±0.40(Predicted)

color 

Slightly Yellowish Crystalline

CAS DataBase Reference

14080-59-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-36

Safety Statements 

26-45

RIDADR 

UN2811

HS Code 

2933599590

4-CHLOROTHIENO[2,3-D]PYRIMIDINE Usage And Synthesis

Chemical Properties

Slightly Yellowish Crystalline Solid

Uses

4-Chlorothieno[2,3-d]pyrimidine (cas# 14080-59-2) is a compound useful in organic synthesis.

Definition

ChEBI: 4-Chlorothieno[2,3-d]pyrimidine is an organic heterobicyclic compound, an organonitrogen heterocyclic compound and an organosulfur heterocyclic compound.

Synthesis

General procedure for the synthesis of 4-chlorothieno[2,3-d]pyrimidine using thieno[2,3-d]pyrimidin-4(3H)-one as starting material: a solution of N,N-dimethylformamide (DMF, 1.53 mL, 19.7 mmol) in dichloromethane (50 mL) was cooled to 0 °C, oxalyl chloride (2.5 mL, 29.6 mmol) was slowly added, and the reaction system formed a A white gel-like substance was formed in the reaction system. Thieno[2,3-d]pyrimidin-4(3H)-one (1.5 g, 9.86 mmol) was then added and the reaction mixture was heated to reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and poured into water. The aqueous phase was extracted with dichloromethane, the organic phases were combined and dried over anhydrous sodium sulfate and subsequently concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=15:1) to afford 4-chlorothieno[2,3-d]pyrimidine as a white solid (1.61 g, 96% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3, 25 °C): δ= 8.88 (s, 1H, CH), 7.64 (d, J = 6.0 Hz, 1H, CH), 7.47 (d, J = 5.8 Hz, 1H, CH) ppm. high-resolution mass spectrometry (HRMS) analysis showed that the calculated value C6H4ClN2S [M]+ 170.97837, measured value 170.97804.

References

[1] Patent: US2012/46278, 2012, A1. Location in patent: Page/Page column 81
[2] Patent: US2014/88088, 2014, A1. Location in patent: Paragraph 1228-1230
[3] Tetrahedron Letters, 2007, vol. 48, # 30, p. 5261 - 5264
[4] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 3, p. 459 - 464
[5] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 31 - 47

4-CHLOROTHIENO[2,3-D]PYRIMIDINE(14080-59-2)Related Product Information

• 4-CHLORO-2,5-DIPHENYLTHIENO[2,3-D]PYRIMIDINE
• 4-CHLORO-5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDINE
• 4-CHLOROTHIENO[2,3-D]PYRIMIDINE
• 4-CHLORO-5-METHYLTHIENO[2,3-D]PYRIMIDINE
• 4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE
• 4-CHLORO-6,7-DIHYDRO-5H-CYCLOPENTA[4,5]THIENO[2,3-D]PYRIMIDINE
• 6-T-BUTYL-4-CHLOROTHIENO[3,2-D]PYRIMIDINE,6-TERT-BUTYL-4-CHLOROTHIENO[3,2-D]PYRIMIDINE
• 4-Chlorothieno[3,2-d]pyrimidine ,97%,4-CHLOROTHIENO[2,3-D]PYRIMIDINE,4-CHLOROTHIENO[3,2-D]PYRIMIDINE
• 6-BROMO-4-CHLOROTHIENO[2,3-D]PYRIMIDINE
• 6-bromo-4-chlorothieno[3,2-d]pyrimidine
• 4-AMINO-2-CHLOROTHIENO[3,2-D]PYRIMIDINE
• 7-BROMO-4-CHLOROTHIENO[3,2-D]PYRIMIDINE
• 2,4-Dichlorothieno[3,2-d]pyrimidine
• 2,4-Dichlorothieno[2,3-d]pyrimidine
• 4-CHLORO-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-D]PYRIMIDINE
• 4-CHLORO-5-(2-THIENYL)THIENO[2,3-D]PYRIMIDINE
• 4-CHLORO-5-(4-NITROPHENYL)THIENO[2,3-D]PYRIMIDINE
• 4-CHLORO-6-METHYL-2,3-DIHYDRO-1H-8-THIA-5,7-DIAZA-CYCLOPENTA[A]INDENE