Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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 C5H4N4
[0120] 5-chloro-2-methoxybenzoic acid (370.0 mg, 1.981 mmol) was dissolved in THF (10.0 mL), followed by the addition of catalytic amount of DMF (20 .iL) and oxalyl chloride (0.20 mL, 2.377 mmol) respectively. The reaction was allowed to stir at rt for 30 mm, concentrated in vacuo, and the residue was re-dissolved in THF (10.0 mL). In another flask, 5-aminopyrazine-2- carbonitrile (170.0 mg, 1.415 mmol) was dissolved in THF (5.0 mL) followed by addition of NaH (85.0 mg, 2.123 mmol, 60% in mineral oil). The mixture was stirred for 10 minutes before it was added to the flask containing the freshly prepared acid chloride dropwise at rt. The reaction was stirred at rt for 30 mm before silica gel was added to quench the reaction. Solvent was evaporated and the resulting residue was purified via silica gel column chromatography to yield 5-chloro-N-(5-cyanopyrazin-2-yl)-2-methoxybenzamide (40.0 mg, 10% yield) which was mixed with pyridinium chloride (550.0 mg). The mixture was heated to 200 C, stirred for 10 minutes and cooled down to rt. The resulting solid was dissolved in water and extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified via silica gel column chromatography to yield 5-chloro-N-(5-cyanopyrazin-2-yl)-2-hydroxybenzamide 3 (27.5 mg, 72% yield). ?H NMR (300 MHz, Acetone-d6) 6 9.70 (d, J= 1.5 Hz, 1H), 8.90 (d, J= 1.5 Hz, 1H), 8.16 (d, J= 2.7 Hz, 1H), 7.59 – 7.51 (m, 1H), 7.17 (d, J= 8.8 Hz, 1H). MS (ESI) exact mass calculated for [M+H] (C12H8C1N402) requires m/z 275.0, found m/z 275.1.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 113305-94-5, its application will become more common.
Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; JIN, Shengkan; AUGERI, David, J.; KIMBALL, David, S.; LIU, Peng; TAO, Hanlin; ZENG, Xiangang; (82 pag.)WO2016/81599; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem