In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 14394-56-0, name is 4-Amino-6-chloro-5-methylpyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 14394-56-0
Example 50 5-methyl-4-N-{1-[3-(pyridin-2-yl)indolizin-2-yl]ethyl}pyrimidine-4,6-diamine To a solution of 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.100 g, 0.42 mmol) in t-BuOH (4.5 mL), 6-chloro-5-methylpyrimidin-4-amine (0.060 g, 0.42 mmol) was added followed by DIPEA (0.146 mL, 0.84 mmol) and the resulting mixture was heated to reflux for 24 h. Additional 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.100 g, 0.42 mmol) was added over 48 h heating to reflux. The solvent was removed and the crude was dissolved in n-BuOH (4.5 mL); DIPEA (0.146 mL, 0.84 mmol) was added and the reaction was heated to 130 C. for 10 days. An additional experiment was performed: to a solution of 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.059 g, 0.25 mmol) in n-BuOH (2.7 mL), 6-chloro-5-methylpyrimidin-4-amine (0.036 g, 0.25 mmol) was added followed by DIPEA (0.087 mL, 0.50 mmol) and the resulting mixture was heated under MW irradiation for 2 h at 120 C. and for 2 h at 150 C. Then the mixture was heated under thermal conditions at 130 C. for 24 h. Additional 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.059 g, 0.25 mmol) was added over 10 days continuing the heating at 130 C. The two reaction mixtures were combined, the solvent was removed and the crude was partitioned between DCM/MeOH 4/1 and water. The organic phase was dried over sodium sulfate, the solvent was removed under reduced pressure and the crude was purified by flash chromatography on Biotage silica-NH cartridge (cyclohexane:EtOAc=50:50 to 40:60); two further purifications by flash chromatography on Biotage silica cartridge (DCM to DCM_MeOH=98:2) were required to afford title compound as a dark yellow solid (0.0207 g). MS/ESI+ 345.2 [MH]+, Rt 0.56 min (Method A). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.78 (d, 1H), 8.69-8.74 (m, 1H), 7.80-7.92 (m, 2H), 7.77 (s, 1H), 7.46 (d, 1H), 7.27-7.35 (m, 1H), 6.76-6.83 (m, 1H), 6.67 (s, 1H), 6.54-6.61 (m, 1H), 6.24-6.33 (m, 1H), 5.85 (br. s., 2H), 5.60-5.70 (m, 1H), 1.80 (s, 3H), 1.41 (d, 3H).
The synthetic route of 14394-56-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; ACCETTA, Alessandro; CAPELLI, Anna Maria; GUALA, Matilde; RETINI, Michele; US2015/361100; (2015); A1;,
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