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. Safety of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
(S)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)(4-(trifluoromethyl)phenyl)methanol: To a mixture of (R)-2,5-dihydro-3,6-dimethoxy-2- isopropylpyrazine (8.0 mL, 45 mmol, Fluka catalog number 37286-5mL) and THF (60 mL) at -78 0C was added n-butyllithium (2.5 M solution in hexane, 19 mL, 47 mmol). The mixture was stirred for 15 minutes. The colorless solution turned light brown. Then a solution of 4-(trifluoromethyl)benzaldehyde (Aldrich, 7.2 mL, 54 mmol) in THF (60 mL) was added dropwise through a dropping funnel at -78 0C. The mixture was stirred for 1 hour after addition was complete. The reaction mixture was diluted with EtOAc and washed with a mixed solution of aqueous Na2HPO4 and KH2PO4 solution (pH ~ 8). The aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The initial product was separated into two isomers by silica gel chromatography (O – 2 percent – 10 percent ACN-DCM). The desired product was obtained as an off-white solid (6.40 g, 40 percent). LCMS (API-ES) m/z (percent): 359 (M++H).
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; AMGEN INC.; ZENG, Qingping; YUAN, Chester Chenguang; YAO, Guomin; WANG, Xianghong; TADESSE, Seifu; ST. JEAN, JR., David J.; REICHELT, Andreas; LIU, Qingyian; HONG, Fang-Tsao; HAN, Nianhe; FOTSCH, Christopher H.; DAVIS, Carl D.; BOURBEAU, Matthew P.; ASHTON, Kate S.; ALLEN, John G.; WO2010/83246; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem