Synthetic Route of 65515-39-1 , The common heterocyclic compound, 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, 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.
(a) 2-methoxy-6-methyl-4-(pent-4-en- -yl)nicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (2.5 g, 15.41 mmol) in THF (80 mL) was added LHMDS (1 M in THF, 16.18 mL, 16.18 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction mixture turned an orange color. The mixture was stirred at 0 C for 50 min, then 4-bromobut-l-ene (1.878 mL, 18.50 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to 10 C for 2.5 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (40 mL) and the layers were separated and the aqueous layer was extracted with EtOAc (3x). The combined organics were concentrated and the residue adsorbed onto silica and purified by flash chromatography (CombiFlash, 0-5% EtOAc in hexane, 80 g column) to afford 2-methoxy-6-methyl-4-(pent-4-en-l-yl)nicotinonitrile (1.3 g, 6.01 mmol, 39.0% yield) as a colorless oil. LC-MS(ES) m/z = 217.0 [M+H]+.
The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
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