Electric Literature of 59303-10-5,Some common heterocyclic compound, 59303-10-5, name is 2-Chloro-5-methylpyrazine, molecular formula is C5H5ClN2, 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.
NaH (60% in mineral oil, 103 mg, 2.57 mmol) was added to a stirred solution of l-Boc- 4-hydroxypiperidine (CAS: 109384-19-2; 470 mg, 2.33 mmol) in DMF (10 mL) at 0 C under N2 atmosphere. The mixture was stirred at room temperature for 1 h. 2-Chloro-5- methylpyrazine (CAS: 59303-10-5; 300 mg, 2.33 mmol) was added to the mixture under N2 atmosphere and the reaction mixture was stirred at 50 C for 16 h. A solution of 1- Boc-4-hydroxypiperidine (CAS: 109384-19-2) in DMF which was stirred for 1 h at room temperature was added, and the reaction mixture was stirred at 80 C for another 16 h. The mixture was diluted with water and extracted with DCM. The organic layer was dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 80:20). The desired fractions were collected and concentrated in vacuo to afford intermediate 151 (320 mg, 47%) as a white solid.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5-methylpyrazine, its application will become more common.
Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; DELGADO-JIMENEZ, Francisca; CONDE-CEIDE, Susana; VEGA RAMIRO, Juan, Antonio; (245 pag.)WO2019/243530; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem