Synthetic Route of 769-27-7 , The common heterocyclic compound, 769-27-7, name is 6-Amino-2,4-dimethylnicotinonitrile, molecular formula is C8H9N3, 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.
EXAMPLE 15 ( )-6-((4-Amino-8-(4-(2-cyanovinyl)-2,6-dimethylphenyl)quinazolin-2-yl)amino)-2,4- dimethylnicotinonitrile- Compound 15 Synthesis of (£)-6-((4-amino-8-(4-(2-cyanovinyl)-2,6-dimethylphenyl)quinazolin-2- yl)amino)-2,4-dimethylnicotinonitrile (compound 15) Compound 15 [0279] Compound 2a (20 mg, 0.06 mmol), 6-amino-2,4-dimethylnicotinonitrile (26 mg, 0.18 mmol, Key Organics Ltd, 1X-0933), N,N-diisopropylethylamine (622 mg, 0.48 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4 mg, 0.006 mmol) and palladium (II) acetate (1 mg, 0.006 mmol) were combined under argon in N-methyl-2- pyrrolidone (1 mL). The reaction was heated at 120C in a sealed vessel for 4 hours. The reaction mixture was cooled down to room temperature and diluted with water and ethyl acetate. The organic layer was separated and washed twice with brine, dried over magnesium sulfate and this solution was filtered through a 2 cm layer of silica gel which was washed with additional ethyl acetate. Combined organics were concentrated down under reduced pressure. The crude residue was treated with diethyl ether in the sonic bath for 5 minutes. The solid compound was filtered off and washed twice with diethyl ether and once with hexane to afford the title compound 15. NMR (400 MHz, DMSO-i/6) delta 9.56 (bs, 1 H), 9.29 (bs, 1 H), 8.44 (d, J = 8.0 Hz, 1 H), 7.99 – 7.47 (m, 5H), 7.41 -7.10 (m, 1 H), 6.55 (d, J = 16.7 Hz, 1 H), 2.41 (bs, 3H), 1.96 (s, 6H), 1.62 (bs, 3H). LCMS (m/z) 446.4 [M+H], Tr = 1.19 min (LCMS method 3).
The synthetic route of 769-27-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GILEAD SCIENCES, INC.; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, V.V.I.; JANSA, Petr; SIMON, Tetr; LANSDON, Eric; HU, Yunfeng, Eric; BASZCZYNSKI, Ondrejj; DEJMEK, Milan; MACKMAN, Richard, L.; (185 pag.)WO2016/105564; (2016); A1;,
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