Category: 58139-03-0

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. 58139-03-0, name is 2-Iodo-6-methoxypyrazine, A new synthetic method of this compound is introduced below., Formula: C5H5IN2O

2. 3-[2-(6-Methoxypyrazin)yl]-1-azabicyclo[2.2.2]octan-3-ol t-Butyllithium (20 ml of a 1.7M solution in pentane, 35.3 mmol) was added dropwise to a rapidly stirred solution of 2-methoxy-6-iodopyrazine (4.17 g, 17.6 mmol) in ether (80 ml), at -40° C. After 0.25 h a solution of quinuclidinone (2.21 g, 17.6 mmol) in ether (60 ml) was added dropwise and the reaction mixture warmed to room temperature and stirred for 2 h. Water (35 ml) was added and extracted with ethylacetate (4*100 ml). The combined extracts were dried (Na2 SO4), the solvent removed under vacuum and, the residue chromatographed through alumina, eluding with dichloromethane/methanol (93:7) to give 3-[2-(6-methoxypyrazin)yl]-1-azabicyclo [2.2.2]octan-3-ol (1.65 g); delta (360 MHz, CDCl3) 1.37-1.51 (3H,m, –CH2 and CH of CH2); 1.70-1.90(1H, brs, OH); 1.94-1.96-(1H,m,CH); 2.20-2.32(1H,m,CH of CH2); 2.80-3.10(5H,m,2*CH2 and CH of CH2) 3.74(1H,dd, J=2 and 14.6 Hz, CH of CH2); 3.99(3H,s,Me); 8.15(1H,s,pyrazine-H); 8.39(1H,s,pyrazine-H).

The synthetic route of 58139-03-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; US5260293; (1993); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 58139-03-0, name is 2-Iodo-6-methoxypyrazine, 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. Computed Properties of C5H5IN2O

1. 3-[2-(6-Methoxypyrazin)yl]-3-hydroxy-1-azabicyclo-[2.2.1]heptane t-Butyllithium (24 ml of a 1.7M solution in pentane, 40.8 mmol) was added dropwise to a rapidly stirred solution of 2-iodo-6-methoxypyrazine (4.7 g, 19.9 mmol) in ether (125 ml), at -50° C. The reaction mixture was stirred for 0.25 h and a solution of 1-azabicyclo[2.2.1]heptan-3-one (2.86 g, 25.8 mmol) in ether (20 ml) (predried over MgSO4), then added and warmed to room temperature. Aqueous workup and extraction into dichloromethane gave the crude product which was chromatographed on alumina using dichloromethane/methanol (96:4) as eluant to give the title alcohol (2.91 g) as a yellow oil; (Found: M+ =221.1166; C11 H15 N3 O2 requires M+ =21.1164); m/e 221 (M+); delta(250 MHz, CDCl3) 1.46-1.62 (1H, m, CH of CH2); 2.26-2.40 (1H, m, CH of CH2); 2.50 (1H, dd, J=3.5 and 12 Hz, CH of CH2 –N); 2.60 (1H, dd, J=4.5 and 14 Hz, CH of CH2 –N); 2.72 (1H, d, J=4.5 Hz, CH-bridgehead); 2.74-3.06 (2H, m, CH2 –N); 3.07-3.14 (1H, m, CH of CH2 –N); 3.42 (1H, dd, J=1.5 and 14 Hz, CH of CH2 –N); 3.96 (3H, s, OMe); 8.13 (1H, s, pyrazine-H); 8.37 (1H, s, pyrazine-H).

The synthetic route of 2-Iodo-6-methoxypyrazine has been constantly updated, and we look forward to future research findings.