Synthetic Route of 50866-30-3, These common heterocyclic compound, 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, 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 of N,Nbis(4-methoxybenzyl)ethanesulfonamide (Example 12.0, 73.13 g, 0.209 mol, 1.2 equiv.) in anhydrous THF (600 mL) at -78 C was added n-butyl lithium (83.71 mL, 0.209 mol, 2.5 M solution in hexanes, 1.2 equiv.) via additional funnel slowly, and the resulting mixture was stirred for 10 mm. Then a solution of 5-methylpyrazine-2-carbaldehyde (Example 33.1, 21.3 g, 0.174 mol, 1.0 equiv.) in anhydrous THF (150 mL) was added, and the resulting mixture was stirred at the same temperature for 45 mm and then allowed to warm to RT for 2 h. The reaction mixture was quenched by the addition of aqueous ammonium chloride (200 mL) and extracted with EtOAc (2 x 2 L). The combined organic layers were washed with brine (2 x 500 mL) (Note: no productwas observed in the ammonium chloride or brine layer). After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo, to afford an oil. The oil was purified by flash column chromatography (silica gel, 23 0-400 mesh) to afford the two isomers. The faster moving isomer (32 g as a white solid) was obtained from the column with a gradient of 10 % to 30 % EtOAc in petroleum ether. 1H NMR (400 MHz, DMSO-d6) 0 8.61 (d, J 1.5 Hz, 1H), 8.51 (d, J= 1.5 Hz, 1H), 7.22-7.11 (m, 4H), 6.90-6.80 (m, 4H), 6.10 (d, J= 5.9 Hz, 1H), 5.29 (dd,J= 5.9, 2.2 Hz, 1H), 4.36-4.16 (m, 4H), 3.73 (m, 6H), 3.70-3.66(m, 1H) 2.50 (merged with solvent peak, 3H) and 1.10 (d,J= 7.0 Hz, 3H). LCMS-ESI (pos.) m/z:472.4 (M+H)t; Further elution of themixture with a gradient of 30 % to 35 % EtOAc in petroleum ether yielded Example 33.3 (16 g, pale yellow gummy liquid). 1H NMR (400 MHz, CDC13) oe 8.62 (d, J= 1.6 Hz, 1H), 8.44 (d,J= 1.5 Hz, 1H), 7.25-7.12 (m, 4H), 6.93-6.82 (m, 4H), 5.17 (d,J= 7.1 Hz, 1H), 4.47 (d, J= 15.2 Hz, 3H), 4.14 (d, J 15.4 Hz, 2H), 3.82 (d, J 1.8 Hz, 6H), 3.66-3.61 (m, 1H), 2.60 (d, J = 2.0 Hz, 3H), and 1.08 (dd, J = 7.2, 2.1 Hz, 3H). LCMSESI (pos.) m/z:472.4 (M+H)t
Statistics shows that 5-Methylpyrazine-2-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 50866-30-3.
Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; (434 pag.)WO2018/93577; (2018); A1;,
Pyrazine – Wikipedia,
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