Electric Literature of 349-75-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 349-75-7 as follows.
General procedure: An alcohol(2.25±6.1 equiv) was added dropwise to a cooled suspension of NaH (60% dispersion in mineraloil; 2.2±6 equiv) in dry THF (0.5±1.5 mL) at 0 C and the mixture was stirred for 1 hunder argon atmosphere. A solution of 10 in dry THF (0.5±1.5 mL) was added dropwise andmixture was stirred overnight letting to warm up to rt. The reaction was quenched with icewater and acidified with a solution of KHSO4 until pH3. The aqueous phase was extractedwith EtOAc. The combined organic layers were washed with brine and the solvent was evaporatedunder reduced pressure at 40 C. The crude residue was purified by flash column chromatographywith appropriate eluents and a gradient.Heptyl 6-(heptyloxy)-2-[(4-methoxyphenoxy)methyl]-5-methylpyrimidine-4-carboxylate(11). General procedure III was followed except that the mixture containing the alkoxidewas added dropwise to the solution of 10. NaH (60% in mineral oil; 69.2 mg, 1.73 mmol, 2.2equiv), dry THF (1.25 mL), 1-heptanol (0.250 mL, 1.77 mmol, 2.25 equiv); compound 10(0.300 g, 0.787 mmol), dry THF (1.25 mL). Flash chromatography eluents: cyclohexane (A),EtOAc (B); gradient: 10%30% B×15 CV. Compound 11 was isolated as an orange oil (46.6mg, 0.0958 mmol, 12.2% yield).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,349-75-7, its application will become more common.
Reference:
Article; Provenzani, Riccardo; Tarvainen, Ilari; Brandoli, Giulia; Lempinen, Antti; Artes, Sanna; Turku, Ainoleena; Jaentti, Maria Helena; Talman, Virpi; Yli-Kauhaluoma, Jari; Tuominen, Raimo K.; Boije af Gennaes, Gustav; PLoS ONE; vol. 13; 4; (2018);,
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