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| | 4-Chloro-6-ethyl-5-fluoropyrimidine Basic information |
| | 4-Chloro-6-ethyl-5-fluoropyrimidine Chemical Properties |
| Boiling point | 211°C | | density | 1.286 | | Fp | 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) |
| | 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 Preparation Products And Raw materials |
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