| Identification | More | [Name]
Ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate | [CAS]
720-01-4 | [Synonyms]
BUTTPARK 43\57-70
ETHYL 4-CHLORO-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
4-Chloro-2-trifluoromethyl-pyrimidine-5-carboxylic acid ethyl ester
Ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate 97%
Ethyl4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate97% | [EINECS(EC#)]
672-018-2 | [Molecular Formula]
C8H6ClF3N2O2 | [MDL Number]
MFCD00173897 | [Molecular Weight]
254.59 | [MOL File]
720-01-4.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection . | [Hazard Note ]
Irritant | [HS Code ]
29335990 |
| Hazard Information | Back Directory | [Uses]
Ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate is used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.
| [Synthesis]
General procedure for the synthesis of ethyl 2-trifluoromethyl-4-chloropyrimidine-5-carboxylate using ethyl 4-hydroxy-2-trifluoromethylpyrimidine-5-carboxylate as starting material:
1. ethyl 4-hydroxy-2-trifluoromethylpyrimidine-5-carboxylate (51.8 g) was dissolved in dichloromethane (600 mL) under ice bath conditions.
2. Oxalyl chloride (57.4 mL) was slowly added to the above solution, followed by dimethylformamide (0.2 mL) as a catalyst.
3. The reaction mixture was stirred at room temperature for 16 hours.
4. Upon completion of the reaction, the solvent was removed by rotary evaporator.
5. Toluene was added and evaporated again to completely remove residual oxalyl chloride and by-products.
6. The residue is redissolved in methylene chloride and the organic layer is washed with water to remove water-soluble impurities.
7. The organic layer was dried using anhydrous magnesium sulfate, filtered and concentrated by rotary evaporator to afford the title compound ethyl 2-trifluoromethyl-4-chloropyrimidine-5-carboxylate as an orange oil (55.7 g, 100% yield).
Product characterization data:
1H-NMR (CDCl3) δ 9.25 (1H, s), 4.51 (2H, q), 1.46 (3H, t);
13C-NMR (CDCl3) δ 126.0 (2C), 161.1, 158.1 (q, J = 39 Hz), 127.0, 118.9 (q, J = 276 Hz), 63.5, 14.4. | [References]
[1] Patent: US2004/167142, 2004, A1. Location in patent: Page/Page column 23
[2] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1645 - 1648 |
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