Synthetic Route of 486424-37-7, The chemical industry reduces the impact on the environment during synthesis 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.
Step 1: 3-Amino-6-bromo-N-methoxy-N-methyl pyrazi ne-2-carboxamideTo a stirred suspension of 3-amino-6-bromopyrazine-2-carboxylic acid (45 g, 206 mmol) andO,N-dimethylhydroxylamine hydrochloride (20.13 g, 206 mmol) in DMF (295 mL) at RT wasadded triethylamine (115 mL, 826 mmol) under N2 supply. The resulting mixture was cooledto 0C and to this yellow suspension T3P (50 % in EtOAc) (151 g, 237 mmol) was added dropwise over 5 mm (keeping T below 10C – exotherm). The mixture was allowed to warm to RT and stirred for 2-3 hours. During the reaction the contents had set solid into a gel. The flask was diluted with a further 200 ml of DMF and was warmed to 40 C and was leftovernight. Further triethylamine (50 mL, 0.4 equiv), O,N-dimethylhydroxylamine hydrochloride (10 g, 0.5 equiv) and T3P (80 g, 0.5 equiv) were added and the reaction mixture was warmed to 4000 and was allowed to stir for 2-3 hours. The mixture was allowed to cool to RT and then stirred for three days. The mixture was worked up by the addition of 2M HCI (100 mL) and was diluted with ethyl acetate (1 L) and water (500 mL). The biphasic mixture was separated. The aqueous layer was basified with 2M NaOH (- 150 mL), organicextract was added back and the biphasic mixture was shaken. The organic was extracted, washed with brine, dried over MgSO4, filtered and dried under vacuum to give a yellow oil. The crude yellow oil was loaded directly onto a 750 g column (in DCM 20 mL) and was eluted with iso-Hex / EtOAc (0- 70 % gradient). The fractions containing pure product were combined and evaporated to give a yellow oil. Diethyl ether (50 mL) was added and this wasevaporated under vacuum to give a pale yellow solid;LC-MS: Rt 0.88 mins; MS m/z 263.1 MH+; Method 2minLC_v003
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Amino-6-bromopyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem