New learning discoveries about Ethyl 4-chloropyrimidine-5-carboxylate

At the same time, in my other blogs, there are other synthetic methods of this type of compound,41103-17-7, Ethyl 4-chloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 41103-17-7, Ethyl 4-chloropyrimidine-5-carboxylate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, HPLC of Formula: C7H7ClN2O2, blongs to pyrimidines compound. HPLC of Formula: C7H7ClN2O2

To a stirred solution of ethyl 4-chloropyrimidine-5-carboxylate (1 g, 5.35 mmol) in toluene (50 mL) under an inert atmosphere was added cyclopropylboronic acid (829 mg, 9.64 mmol) and cesium carbonate (2.62 mg, 8.03 mmol) at room temperature in a sealed tube. The reaction mixture was degassed under argon for 15 min. Pd(dppf)Cl2 (218 mg, 0.26 mmol) was added at room temperature and the solution was degassed under argon for another 10 min. The reaction mixture was heated to 100 C. and stirred for 5 h. After consumption of starting material (by TLC), the reaction mixture was filtered through a pad of celite, and the pad was washed with EtOAc (100 mL). The filtrate was concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluent: 20% EtOAc/Hexane) to afford ethyl 4-cyclopropylpyrimidine-5-carboxylate (150 mg, 0.78 mmol, 15%) as a pale yellow syrup. 1H NMR (400 MHz, DMSO-d6): delta 9.08 (s, 1H), 8.98 (s, 1H), 4.37 (q, J=7.1 Hz, 2H), 3.01-2.93 (m, 1H), 1.35 (t, J=7.1 Hz, 3H), 1.18-1.15 (m, 4H) LC-MS: m/z 192.9 [M+H]+ at 2.40 RT (95.93% purity)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,41103-17-7, Ethyl 4-chloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; (93 pag.)US2018/186773; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia