Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, A new synthetic method of this compound is introduced below., Product Details of 50866-30-3
A vial was charged with C65 (100 mg, 0.33 mmol), and the vial was evacuated and flushed with nitrogen; this procedure was repeated twice, tetrahydrofuran (1.6 mL) was added, and the solution was cooled to -78 C. 2,2,6,6-Tetramethylpiperidinylmagnesium chloride, lithium chloride complex (1 M solution in tetrahydrofuran and toluene; 0.497 mL, 0.497 mmol) was added, and the reaction mixture was allowed to stir for 1 hour at -78 C. In a separate vial, 5-methylpyrazine-2- carbaldehyde (80.9 mg, 0.662 mmol) was dissolved in tetrahydrofuran (1.6 mL), and the resulting solution was cooled in a dry ice/acetone bath for 10 minutes. This solution wasthen added to the reaction mixture, which was subsequently allowed to stir while slowly warming to 15 C. After 1 hour, it was combined with two similar reaction mixtures derived from C65 (50 mg, 0.17 mmol; 100 mg, 0.33 mmol), and the resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 x 15 mL). The combined organic layers were concentrated in vacuo and subjected to reversed-phaseHPLC (Column: Phenomenex Synergi Max-RP, 10 pm; Mobile phase A: 0.1% trifluoroacetic acid in water; Mobile phase B: acetonitrile; Gradient: 15% to 45% B), affording a diastereomeric mixture of 14 and 15 as a viscous, brick-red oil. Combined yield of diastereomeric mixture: 180 mg, 0.425 mmol, 51%. This material was separated into its component diastereomers via supercritical fluid chromatography [Column: Regis Technologies, (S,S)-Whelk-O 1, 10 pm; Mobile phase: 3:2 carbon dioxide I (ethanol containing 0.1 % ammonium hydroxide)]. The firsteluting diastereomer, obtained as a light yellow solid, was designated as 14. Yield: 58.6mg, 0.138 mmol, 32% for the separation. LCMS m/z 423.9 (chlorine isotope pattern observed) [M+H]. 1H NMR (400 MHz, CD3OD) 9.12 (br s, 1 H), 8.92 (5, 1 H), 8.83-8.74 (brs, 1H), 8.48 (5, 1H), 8.18 (d, J=9.0 Hz, 1H), 7.74 (dd, J=9.0, 2.0 Hz, 1H), 6.51 (5, 1 H), 5.58-5.46 (m, 1 H), 4.29 (dd, J=1 1.8, 5.3 Hz, 1 H), 3.80-3.66 (br m, 1 H), 3.66-3.52 (br m, 1H), 2.79-2.66 (m, 1H), 2.60 (5, 3H), 2.42-2.27 (br m, 1H), 2.13-2.00 (br m, 1H),1.77-1.63 (brm, 1H), 1.28 (brd, J=5.5 Hz, 3H).The second-eluting diastereomer, also isolated as a light yellow solid, was designated as 15. Yield: 56.8 mg, 0.134 mmol, 32% for the separation. LCMS m/z 423.9 (chlorine isotope pattern observed) [M+H]. 1H NMR (400 MHz, CD3OD) 9.12 (br s, 1 H), 8.92 (5, 1 H), 8.82-8.74 (br s, 1 H), 8.47 (br s, 1 H), 8.18 (d, J=8.5 Hz, 1 H),7.74 (dd, J=9.0, 2.0 Hz, 1H), 6.50 (5, 1H), 5.57-5.46 (m, 1H), 4.21 (dd, J=11.8, 4.8 Hz,1 H), 3.82-3.70 (br m, 1 H), 3.62-3.47 (br m, 1 H), 2.71-2.57 (br m, 1 H), 2.59 (5, 3H),2.48-2.35 (m, 1H), 2.24-2.13(brm, 1H), 1.63-1.50 (brm, 1H), 1.34(d, J=6.0 Hz, 3H).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; CHAPPIE, Thomas Allen; CHEN, Jinshan Michael; COE, Jotham Wadsworth; COFFMAN, Karen Jean; GALATSIS, Paul; GARNSEY, Michelle Renee; HELAL, Christopher John; HENDERSON, Jaclyn Louise; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G.; MARTINEZ-ALSINA, Luis Angel; PETTERSSON, Martin Youngjin; REESE, Matthew Richard; ROSE, Colin Richard; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; WARMUS, Joseph Scott; ZHANG, Yuan; (193 pag.)WO2018/163066; (2018); A1;,
Pyrazine – Wikipedia,
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