Application of 851984-15-1 , The common heterocyclic compound, 851984-15-1, name is 6-Chloro-5-fluoropyrimidin-4-amine, molecular formula is C4H3ClFN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a solution the Boc protected amine 31.15 (1 eq) was in 1 ,4-dioxane (50 eq) was added HC1 (4 N in 1 ,4 dioxane 15 eq) and the solution was heated to 60 oC for 60 min. The solvent was removed in vacuo and the crude amine (1.0 eq) was dissolved in 1 -butanol (100 eq) and treated with 6-chloro-5-fluoropyrimidin-4- amine (1.5 eq) and DIPEA (10.0 eq). The reaction solution was stirred at 1 10 C for 16 h, cooled to rt and diluted with EtOAc (20 mL), washed with H20 (10 mL), saturated brine (10 mL), dried ( a2S04), filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (Petroleum ether/EtOAc 1/1) to give the desired product compound 279 as light yellow solid (63% yield).1.. NMR (400 MHz, CDC13) delta 7.93 (br. s., 1H), 6.44 (br. s., 1H), 6.39 (br. s., 1H), 6.23 (br. s., 1H), 4.71 (m, 1H), 4.01 (m, 1H), 3.82 (m, 1H), 3.40 (br. s., 1H), 3.17 – 3.23 (m, 1), 2.47 (br. s., 1H), 2.35 (s, 2H), 2.35 (m, 1H), 2.03 (br. s., 2H), 1.60 (br. s., 1H). EIMS (m/z): calcd. for C2oH22ClF3 60 (M+) 454.8, found 454.8.
The synthetic route of 851984-15-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); A1;,
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