These common heterocyclic compound, 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, its 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. category: chlorides-buliding-blocks
To a solution of 3, 6-dichloro- 1,2,4,5 -tetrazine (2.67 g, 17.7 mmol) in methyl ter/-butyl ether (125 mL) at -25 C under nitrogen was added but-3-yn-l -amine hydrochloride (1.87 g, 17.7 mmol), followed by the addition of N,N-diisopropylethylamine (12.4 mL, 70.7 mmol) and the reaction mixture was stirred at -25 C under nitrogen for 26 h. Silica gel (-5 g) was added to the reaction and all solvents were removed in vacuo. The silica gel mesh was loaded on an ISCO silica gel cartridge (220 g) eluting with 25% (0558) EtOAc/hexanes over 2592 mL to afford the title compound (853.3 mg) as a deep red/orange viscous oil,. NMR (400 MHz, CDCh) delta 6.12 (br s, 1H), 3.80 (q, J=6.3 Hz, 2H), 2.63 (td, J=6.3, 2.6 Hz, 2H), 2.10 (t, J=2.6 Hz, 1H).
The synthetic route of 3,6-Dichloro-1,2,4,5-tetrazine has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
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