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.
Synthetic Route of 914452-71-4, A common heterocyclic compound, 914452-71-4, name is 2-Bromo-6-methylpyrazine, molecular formula is C5H5BrN2, 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.
n-Butyllithium (2.5M solution in hexane, 2.57 mL, 6.43 mmol) was added dropwise to 2-bromo-6-methylpyrazine (1060 mg, 6.13 mmol) in DCM (6 mL) at -78 C under nitrogen. 4H-spiro[benzo[d]isoxazole-7,1′-cyclopropan]-5(6H)-one (500 mg, 3.06 mmol) in DCM (1.5 mL) was added dropwise after the mixture had been stirred for 30 min. The mixture was stirred at -78 C for 1.5 h under 2, quenched with sat. aq. NaHCCb (20 mL) and extracted with DCM (3 x 20 mL). The combined organic layers were washed with brine (1 x 25 mL), dried over Na2S04, fdtered and evaporated. The crude product was purified by silica gel chromatography (45 to 50% EtOAc in petroleum ether). Pure fractions were evaporated to dryness to afford 5-(6-methylpyrazin-2-yl)-5,6-dihydro-4H-spiro[benzo[d]isoxazole-7,1′-cyclopropan]-5-ol (200 mg, 25.4 %) as a yellow foam. XH NMR (400 MHz, CDCb) d ppm 0.58 (ddd, J = 9.2, 7.3, 4.0 Hz, 1H), 1.01 (ddd, J = 9.1, 7.3, 4.0 Hz, 1H), 1.35 (ddd, J = 9.8, 7.3, 3.9 Hz, 1H), 1.76 (ddd, J= 9.9, 7.3, 3.9 Hz, 1H), 2.58 (d, J= 7.5 Hz, 1H), 2.61 (s, 3H), 2.63 (d, J = 4.4 Hz, 1H), 2.85 (dd, J = 16.0, 1.5 Hz, 1H), 3.22 (d, J = 16.0 Hz, 1H), 4.14 (s, 1H), 8.13 (s, 1H), 8.45 (s, 1H), 8.61 (s, 1H). m/z (ES+), [M+H]+ = 258; HPLC (C05)tR = 0.663 min (92.3%).
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; MEDIMMUNE LIMITED; BARTHOLOMEUS, Johan; BUeRLI, Roland; JARVIS, Rebecca; JOHNSTONE, Shawn; OSTENFELD, Thor; TERSTIEGE, Ina; TRAVAGLI, Massimiliano; TURCOTTE, Stephane; (203 pag.)WO2019/122265; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem