Category: 181284-14-0

Some common heterocyclic compound, 181284-14-0, name is 3-Chloro-5-methylpyrazine-2-carbonitrile, molecular formula is C6H4ClN3, 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. HPLC of Formula: C6H4ClN3

To a solution of 3-chloro-5-methylpyrazine-2-carbonitrile (19 g, 0.12 mol) and methyl 2-mercaptoacetate (14 g, 0.13 mol) in THF (200 mL) was added NaH (60% dispersion in mineral oil; 7.5 g, 0.19 mol) in small portions at 0 C. The reaction mixture was stirred overnight at RT and then water (200 mL) was carefully added to quench the reaction. The resulting mixture was extracted with ethyl acetate (2 x 300 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified via silica gel column chromatography eluting with petroleum ether / EtOAc (90: 10 to 70:30) to afford methyl 7-amino-3-methylthieno[2,3-6]pyrazine-6-carboxylate (20 g, 72%> yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-fifc): delta 8.68 (s, IH), 7.10 (br s, 2H), 3.83 (s, 3H), 2.65 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 181284-14-0, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA, JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E.R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (113 pag.)WO2017/139779; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 181284-14-0,Some common heterocyclic compound, 181284-14-0, name is 3-Chloro-5-methylpyrazine-2-carbonitrile, molecular formula is C6H4ClN3, 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.

[00683] 3-Chloro-5-methylpyrazine-2-carbonitrile (1.1 g, 0.007 mol) was dissolved in anhydrous DMF (11 mL) and DIPEA (3.74 mL, 0.021 mol) was added. After stirring for 30 min at room temperature tert-butyl (4-methylpiperidin-4-yl)carbamate (1.84 g, 0.008 mol) was added in one portion. The reaction mixture was stirred overnight at room temperature, then diluted with EtOAc and extracted with 2% NaCl (aq.). The organic layer was dried over Na2SC4 and concentrated under reduced pressure. The desired product was purified via column chromatography (DCM/acetone 97:3) to yield tert-butyl N-[l-(3-cyano-6- methylpyrazin-2-yl)-4-methylpiperidin-4-yl]carbamate as a pale yellow solid (2.14 g, 90%). 1H MR (400 MHz, DMSO-i) delta 7.97 (s, 1H), 6.67 (bs, 1H), 3.96 (dt, J = 13.7, 4.3 Hz, 2H), 3.39 (dd, J = 13.4, 10.3 Hz, 2H), 2.42 (s, 3H), 2.15 (d, J = 13.4 Hz, 2H), 1.51 (ddd, J = 14.1, 10.6, 3.9 Hz, 2H), 1.40 (s, 9H), 1.27 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-5-methylpyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; REVOLUTION MEDICINES, INC.; BLANK, Brian R.; PITZEN, Jennifer; WANG, Gang; WON, Walter S.; TZITZILONIS, Christos; LI, Jie Jack; KOLTUN, Elena S.; AAY, Naing; BUCKL, Andreas; MELLEM, Kevin; SEMKO, Christopher; JOGALEKAR, Ash; KISS, Gert; GILL, Adrian; (298 pag.)WO2018/136265; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem