4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine Chemical Properties

Melting point:

196-197 °C

Boiling point:

271.7±40.0 °C(Predicted)

Density 

1.322±0.06 g/cm3(Predicted)

storage temp. 

-20°C, sealed storage, away from moisture

form 

solid

pka

1.07±0.20(Predicted)

color 

Brown to reddish brown

Safety Information

HazardClass 

IRRITANT

HS Code 

2933599590

4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-one from 1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-4-one: 11 mL of phosphorochloride was added to 6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (1.56 g, 11.4 mmol) made in step C. The mixture was stirred under reflux conditions for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature. Subsequently, dichloromethane (DCM) was added to the reaction solution and diluted with water. The aqueous layer was extracted with DCM, and after combining the organic layers, it was purified by column chromatography to finally obtain 4-chloro-6,7-dihydro-5H-cyclopentapyrimidine (1.67 g, 95% yield). The product was characterized by 1H-NMR (DMSO-d6): δ 8.78 (1H, s), 3.03 (2H, t), 2.99 (2H, t), 2.10 (2H, m).

References

[1] Patent: EP3239143, 2017, A2. Location in patent: Paragraph 0500
[2] Patent: WO2008/6040, 2008, A1. Location in patent: Page/Page column 40; 95