Some common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, molecular formula is C9H16N2O2, 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. name: (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
Step C – Synthesis of Intermediate Compound Int-7cTo a solution of (i?)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (6.16 g, 33.4 mmol) in THF (60 mL) was added TBAI (617 mg, 1.67 mmol). The mixture was cooled to -78 °C and a solution of rc-BuLi (14.7 mL, 2.5M in hexanes, 36.75 mmol) was slowly added over 10 minutes. The reaction mixture was allowed to stir at -78 °C for 30 minutes, then Int-7b in THF (20 mL) was slowly added over 10 minutes. The reaction was allowed to stir at -78 °C for 2 hours then allowed to warmed to room temperature and allowed to stir for about 15 hours. The reaction was quenched by addition of MeOH (5 mL), concentrated in vacuo, water added (50 mL) followed by diethyl ether (50 mL) and the layers were separated. The organic layer was washed with water (2 x 50 mL) then dried over Na2S04, filtered and concentrated in vacuo to provide the crude product. Further purification by column chromatograpy on a 330 g ISCO Redi-Sep silica gel column using a eluent of CH2C12 with a gradient of 0-10percent EtOAc/hexanes afforded the desired product Int-7c as a light amber oil (8.65 g, 63percent). 1H NMR (CDC13) ? 4.07-3.99 (m, 1H), 3.94- 3.89 (m, 1H), 3.79-3.71 (m, 2H), 3.68-3.63 (m, 6H), 2.32-2.17 (m, 1H), 1.25-1.21 (m, 1H), 1.06-0.95 (m, 5H), 0.88 (s, 10H), 0.74-0.68 (m, 1H), 0.69-0.66 (m, 2H), 0.12-0.02 (m, 12H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 109838-85-9, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; DWYER, Michael, P.; KEERTIKAR, Kartik, M.; ZENG, Qingbei; MAZZOLA, Robert, D., Jr.; YU, Wensheng; TANG, Haiqun; KIM, Seong Heon; TONG, Ling; ROSENBLUM, Stuart, B.; KOZLOWSKI, Joseph, A.; NAIR, Anilkumar Gopinadhan; WO2013/39876; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem