4-Chloro-6-ethyl-5-fluoropyrimidine Chemical Properties

Boiling point:

211°C

Density 

1.286

Flash point:

81°C

refractive index 

1.496

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Ethyl Acetate

pka

-0.45±0.26(Predicted)

form 

Oil

color 

Clear Colourless to Pale Yellow

InChI

InChI=1S/C6H6ClFN2/c1-2-4-5(8)6(7)10-3-9-4/h3H,2H2,1H3

InChIKey

LKTGVRWVTAJGMS-UHFFFAOYSA-N

SMILES

C1=NC(CC)=C(F)C(Cl)=N1

CAS DataBase Reference

137234-74-3(CAS DataBase Reference)

Safety Information

Risk Statements 

20/21/22-36/37/38-41

Safety Statements 

22-36/37/39-45-39-26

RIDADR 

UN3267

HazardClass 

8

HS Code 

2933599590

4-Chloro-6-ethyl-5-fluoropyrimidine Usage And Synthesis

Chemical Properties

4-Chloro-6-ethyl-5-fluoropyrimidine is Yellow Liquid

Uses

4-Chloro-6-ethyl-5-fluoropyrimidine is a pyrimidine derivative used as a building block in the preparation of bio-active compounds such as broad-spectrum triazole antifungal agents.

Synthesis

Example 1: Synthesis of 4-chloro-6-ethyl-5-fluoropyrimidine <1-1> Preparation of 4-chloro-6-ethyl-5-fluoropyrimidine 80 g of 6-ethyl-5-fluoropyrimidin-4(3H)-one was dissolved in a solvent mixture of 240 mL of dichloromethane and 57.4 mL of N,N-dimethylformamide. Subsequently, 78.24 mL of triethylamine was added to the solution as a base. Phosphoryl chloride (POCl3) was slowly added dropwise to the reaction system over a period of 30 minutes. The reaction mixture was stirred under reflux conditions for 5 hours to ensure complete reaction, after which it was cooled to room temperature. 352 mL of 3N hydrochloric acid solution was carefully added to the reaction mixture at a controlled temperature not exceeding 20°C. The aqueous phase was extracted with 100 mL of dichloromethane and the organic layers were combined and washed with 100 mL of water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the oily target product 4-chloro-6-ethyl-5-fluoropyrimidine (85.9 g, 95% yield). 1H-NMR (300 MHz, CDCl3) δ (ppm): 8.70 (1H, s), 2.90 (2H, q), 1.34 (3H, t).

References

[1] Patent: WO2009/20323, 2009, A2. Location in patent: Page/Page column 7; 9
[2] Organic Process Research and Development, 2001, vol. 5, # 1, p. 28 - 36
[3] Patent: CN103896855, 2016, B. Location in patent: Paragraph 0023; 0033; 0038; 0039
[4] Patent: WO2007/13096, 2007, A1. Location in patent: Page/Page column 8
[5] Patent: WO2010/95145, 2010, A1. Location in patent: Page/Page column 17-18

4-Chloro-6-ethyl-5-fluoropyrimidine(137234-74-3)Related Product Information

• Voriconazole Impurity 5
• Vortioxetine Impurity 2
• (2RS, 3RS)-2-(2,4-Difluorophenyl)-3-(5-fluoropyriMidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol)
• Voriconazole EP IMpurity E
• Methyl Pyridine Sulfonate
• Vortioxetine Impurity 22
• Vortioxetine Impurity 1
• Vonoprazan Impurity 41
• Voriconazole Impurity 8
• 5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde
• (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride
• (trans)-6-Chloro-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
• 6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine
• Pyrimidine, 4-ethyl- (6CI,8CI,9CI)
• Pyrimidine, 4-chloro-6-(1,1-dibromoethyl)-5-fluoro-
• Voriconazole Impurity 53
• 2-CHLORO-1-(2,6-DIFLUOROPHENYL)ETHAN-1-ONE
• Voriconazole Impurity 18