3934-20-1, A common compound: 3934-20-1, name is 2,4-Dichloropyrimidine,molecular formula is C4H2Cl2N2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
To a stirred solution of 2,4-dichloropyrimidine (3.00 g, 20.1 mmol) in toluene (25 mL) was added 4-fluorophenylboronic acid (2.82 g, 20.1 mmol), potassium carbonate (8.32 g, 60.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.630 g, 0.545 mmol) and 1 : 1 (v/v) ethanol/water (36 mL). The mixture was heated at 55 C for 12 hours and then concentrated. The residue was diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried (Na2S04) and concentrated. The crude material was purified by flash chromatography over silica using a hexane/ethyl acetate eluant to afford 2-chloro-4-(4-fluorophenyl)pyrimidine as a yellow solid (2.50 g, 61%). To a stirred solution of this compound (1.27 g, 6.09 mmol) in N,N-dimethylformamide (8 mL) was added ethyl piperidine-4-carboxylate (0.959 g, 6.10 mmol) and cesium carbonate (2.10 g, 6.44 mmol). The mixture was heated at 100 C for 12 hours and then concentrated. The residue was diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried (Na2S04) and concentrated. The crude material was purified by flash chromatography over silica using a hexane/ethyl acetate eluant to afford ethyl l-(4′-fluoro-[l, -biphenyl]-3-yl)piperidine-4-carboxylate as a yellow oil (1.60 g, 80%>). To a stirred solution of this intermediate (1.60 g, 4.80 mmol) in 1 : 1 (v/v) methanol/water (20 mL) was added solid sodium hydroxide (0.968 g, 24.2 mmol). After 2 hours, the reaction was concentrated. The residue was dissolved in water, made acidic (pH ~6) with the addition of IN hydrochloric acid and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2S04) and concentrated to afford l-(4′-fluoro-[l, -biphenyl]-3-yl)piperidine-4-carboxylic acid as a white solid (1.40 g, 97%). Using General Procedure D and Intermediate 5, this carboxylic acid was subjected to amide coupling to generate the title compound as a white solid (0.118 g, 27%). FontWeight=”Bold” FontSize=”10″ Eta NuMuKappa (500 MHz, CDC13) delta 8.37 (d, J= 5.0 Hz, 1H), 8.07-8.04 (m, 2H), 7.15 (t, J= 9.0 Hz, 2H), 6.89 (d, J= 10.0 Hz, 1H), 5.38 (s, 1H), 4.97-4.95 (m, 2H), 3.02-2.83 (m, 8H), 2.39-2.37 (m, 2H), 1.96-1.51 (m, 13H) ppm. 13C NMR (100 MHz, CDCI3) delta 174.1, 165.3, 163.3, 163.2, 161.7, 158.4, 133.8, 129.0, 128.9, 115.7, 115.5, 105.2, 59.4, 53.1, 47.6, 46.1, 44.6, 43.5, 39.3, 36.1, 28.9, 28.7, 25.1, 24.3, 24.2 ppm. Purity: >96% (214 & 254 nm) LCMS; retention time: 1.44 min; (M+H+) 438.3.
With the rapid development of chemical substances, we look forward to future research findings about 3934-20-1.
Reference:
Patent; GENZYME CORPORATION; BOURQUE, Elyse; CABRERA-SALAZAR, Mario, A.; CELATKA, Cassandra; CHENG, Seng, H.; HIRTH, Bradford; GOOD, Andrew; JANCSICS, Katherine; MARSHALL, John; METZ, Markus; SCHEULE, Ronald, K.; SKERLJ, Renato; XIANG, Yibin; ZHAO, Zhong; LEONARD, John; NATOLI, Thomas; MAKINO, Elina; HUSSON, Herve; BESKROVNAYA, Oxana; WO2014/43068; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
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