6-bromoimidazo[1,2-a]pyrazin-8-amine
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6-bromoimidazo[1,2-a]pyrazin-8-amine
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CAS No:
117718-84-0
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Formula:
C6H5BrN4
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Chemical Name:
6-bromoimidazo[1,2-a]pyrazin-8-amine
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Synonyms:
6-bromoimidazo[1,2-a]pyrazin-8-amine;8-Amino-6-bromoimidazo[1,2-a]pyrazine;Imidazo[1,2-a]pyrazin-8-amine,6-bromo-;2-a]pyrazin-8-aMine;8-bromoimidazo[1,2-a]pyrazin-6-amine
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CAS No:
6-bromoimidazo[1,2-a]pyrazin-8-amine Use and Manufacturing
A mixture of the product from Preparative Example 29 (1.80 g, 6.45 mmol) and concentrated aqueous NH4OH (27.0 mL) was stirred in a closed pressure vessel at 90° C. for 24 hr. The solvent was evaporated and the residue was purified by column chromatography on silica gel with EtOAc. White solid (1.01 g, 73percent) was obtained. LCMS: MH+=213.General procedure: In a pressure tube were mixed 5-bromo-6-chloropyrazin-2-amine (4.32 g, 20.73 mmol), phenylboronic acid (2.78 g, 22.80 mmol, 1 .1 equiv.) and Na2003 (4.39 g, 41 .45 mmol, 2 equiv.) in a4:1 mixture of 1 , 4-dioxane : water (50 mL). The reaction mixture was sparged with argon andPd(PPh3)4 (1 .20 g, 1 .04 mmol, 5 mol%) was then added. The pressure tube was capped andthe reaction mixture was heated at 10000 overnight. After that time, the reaction mixture wascooled down to r.t., filtered and concentrated under reduced pressure. The obtained crude ma-terial was purified by flash chromatography on silica eluting with hexane: EtOAc = 1:0 - 1:1 to lead to the title product as a white solid (2.11 g, 50%). ESI-MS: 206.05 [M+H]+. 1 H NMR (300 MHz, DMSO-d6) 6 7.93 (s, 1 H), 7.66 - 7.59 (m, 2H), 7.47 - 7.32 (m, 3H), 7.00 (br s, 2H).
6-bromoimidazo[1,2-a]pyrazin-8-amine
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