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 the BOC-protected intermediate from Example 2 (32 mg, 0.07 mmol) in 1/1 dichloromethane/ methanol (1 mL) was added a solution of 5-methylpyrazine-2-carbaldehyde (11 mg, 0.09 mmol) in 1/1 dichloromethane/methanol (0.3 mL), followed by acetic acid (20 muL, 0.35 mmol) and the mixture was stirred at 50 C. for 15 minutes. MP-cyanoborohydride resin (327 mg, 0.07 mmol) was added and the mixture was shaken at 50 C. overnight, filtered and concentrated. To the residue was added 4M hydrogen chloride in dioxane (2 mL) and the mixture was shaken at 50 C. for 2 hours. The mixture was concentrated, dissolved in 1:1 dimethylsulfoxide/methanol and purified by preparative HPLC (Phenomenex Luna C8(2) 5 mum 100 AXIA column) eluting with a gradient of 5-100% acetonitrile/0.1% trifluoroacetic acid in water to afford the title compound as the trifluoroacetate salt. 1H NMR (400 MHz, pyridine-d5) delta 12.04 (s, 1H) 8.74 (s, 1H) 8.69 (s, 1H) 8.49-8.51 (m, 1H) 8.46 (s, 1H) 7.18 (d, J=7.32 Hz, 1H) 6.91-6.96 (m, 2H) 4.53 (s, 2H) 3.91-4.03 (m, J=8.55 Hz, 1H) 3.63-3.71 (m, J=8.70, 8.70 Hz, 2H) 3.61 (s, 1H) 3.53-3.60 (m, 1H) 3.47 (t, J=8.39 Hz, 2H) 3.07-3.16 (m, 1H) 2.92 (t, J=8.54 Hz, 2H) 2.44 (s, 3H) 2.19-2.27 (m, J=2.44 Hz, 1H) 1.87-2.11 (m, J=28.08 Hz, 2H) 1.76-1.86 (m, J=14.34 Hz, 1H). MS (ESI) m/z 463 (M+H)+.
The synthetic route of 50866-30-3 has been constantly updated, and we look forward to future research findings.