Synthetic Route of 60025-09-4 ,Some common heterocyclic compound, 60025-09-4, molecular formula is C5H3ClN4, 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.
To a solution of 2-(1-(6-fluoro-4-(2-methoxyethylamino)-3-phenylquinolin-2-yl)ethyl)isoindoline-1,3-dione (73.9 mg, 0.157 mmol) in EtOH (2 mL) was added hydrazine (0.049 mL, 1.574 mmol) and the resulting mixture was heated to 60 C. for 20 min. The reaction mixture was allowed to warm to rt and solid was filtered. The filtrate was concd under reduced pressure and used crude for the next step. To the crude solution of 2-(1-aminoethyl)-6-fluoro-N-(2-methoxyethyl)-3-phenylquinolin-4-amine (25 mg, 0.074 mmol) in BuOH (2 mL) was added DIEA (0.033 mL, 0.189 mmol) and 4-amino-6-chloropyrimidine-5-carbonitrile (24.33 mg, 0.157 mmol) and the resulting mixture was stirred at 110 C. overnight. The reaction mixture was cooled to rt and purified via HPLC.4-Amino-6-(1-(6-fluoro-4-((2-methoxyethyl)amino)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile1H-NMR (400 Hz, CD3OD) delta ppm 1.53 (3H, d, J=7.24 Hz) 3.23 (2H, s) 3.33 (2H, m) 3.41 (2H, m) 4.99 (1H, m) 7.48 (1H, m) 7.64 (3H, m) 7.80 (2H, m) 8.03 (1H, s) 8.08 (1H, dd, J=9.39, 4.89 Hz) 8.22 (1H, dd, J=10.47, 2.64 Hz). Mass Spectrum (ESI) m/e=458 (M+1).4-Amino-6-(((1S)-1-(6-fluoro-4-((2-methoxyethyl)amino)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile1H-NMR (400 Hz, CD3OD) delta ppm 1.30 (d, J=6.46 Hz, 3H) 3.18 (s, 3H) 3.19-3.22 (m, 2H) 3.28-3.31 (m, 2H) 5.25 (q, J=6.65 Hz, 1H) 7.37-7.41 (m, 1H) 7.43-7.47 (m, 1H) 7.48-7.55 (m, 2H) 7.55-7.61 (m, 2H) 7.82 (dd, J=10.76, 2.74 Hz, 1H) 7.94 (s, 1H) 8.01 (dd, J=9.29, 5.58 Hz, 1H). Mass Spectrum (ESI) m/e=458 (M+1).4-Amino-6-(((1R)-1-(6-fluoro-4-((2-methoxyethyl)amino)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile1H-NMR (400 Hz, CD3OD) delta ppm 1.30 (d, J=6.65 Hz, 3H) 3.18 (s, 3H) 3.19 (d, J=1.56 Hz, 0H) 3.21 (d, J=5.28 Hz, 1H) 3.29-3.31 (m, 2H) 5.26 (q, J=6.52 Hz, 1H) 7.37-7.41 (m, 1H) 7.43-7.47 (m, 1H) 7.48-7.54 (m, 2H) 7.55-7.61 (m, 2H) 7.91-7.99 (m, 1H) 8.01 (dd, J=9.19, 5.67 Hz, 1H). Mass Spectrum (ESI) m/e=458 (M+1).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60025-09-4, its application will become more common.
Reference:
Patent; AMGEN INC.; US2010/331306; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia