Electric Literature of 33332-28-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33332-28-4, name is 2-Amino-6-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.
[l-(tert-butoxycarbonyl)-lH-indol-2-yl]boronic acid (2.22 g, 8.49 mmol), 6- chloropyrazin-2-amine (1.00 g, 7.72 mmol), K2CO3 (2.67 g, 19.3 mmol) and Pd(PPh3)4 (180 mg, 0.15 mmol) were mixed in MeCN/water (3.5: 1) and stirred at 85 0C for 20 hours. The reaction mixture was concentrated and the residue was extracted with EtOAc (2x 40 mL) and water (50 mL). The organic layers were combined, dried (Na2SO^, filtered and concentrated to give 2.5 g of a brown solid of tert-butyl 2-(6-aminopyrazin-2-yl)- lH-indole-l-carboxylate. The material was used in the next step without further purification. To tert-butyl 2-(6-aminopyrazin-2-yl)-lH-indole- l-carboxylate (1.1 g, 3.5 mmol) in dry toluene (10 mL) were added methyl 6-chloronicotinate (0.67 g, 3.90 mmol), K2CO3 (7.35 g, 53.2 mmol), (+/-)-BINAP (0.1 1 g, 0.18 mmol) and Pd(OAc)2 (40 mg, 0.18 mmol). The mixture was re fluxed for 50 minutes. The solvent was evaporated and the residue was extracted with EtOAc (2×100 mL) and washed with water/brine (1 : 1 ; 100 mL). The organic layers were combined, dried (Na2Spsi4), filtered and concentrated to give 2 g of crude product. Purification was performed by flash chromatography (1percent NEt3 in DCM-> 1percent NEt3, 1percent MeOH in DCM). This gave tert-butyl 2-(6-{[5-(methoxycarbonyl)pyridin-2- yl]amino}pyrazin-2-yl)-lH-indole- l-carboxylate (620 mg). The material was divided into four microwave tubes (155 mg, 0.35 mmol in each) and dissolved in MeOH. 2M aq NaOH (0.35 mL, 0.70 mmol) was added and the reaction mixture was irradiated in a microwave oven at 1 10 0C for 15 minutes. 6M aq HCl (0.12 mL, 0.70 mmol) was added. The reactions were combined and concen- trated in vacuo to give the crude title compound as a brown solid (720 mg). MS (ESI+) for C18H 13N5O2 m/z 332 (M+H)+.
The chemical industry reduces the impact on the environment during synthesis 2-Amino-6-chloropyrazine. I believe this compound will play a more active role in future production and life.
Reference:
Patent; BIOVITRUM AB (PUBL); WO2007/147874; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem