Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 5305-45-3, name is 4,6-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., category: pyrimidines
A mixture of (S)-1-(7-fluoro-2-(pyridin-2-yl)quinolin-3-yl)ethanamine (85 mg, 0.32 mmol), 4,6-dichloro-5-cyanopyrimidine (55 mg, 0.32 mmol, 1.0 eq) and N,N-diisopropylethylamine (68 mul, 0.38 mmol, 1.2 eq) in THF (3 mL) was stirred at rt for 30 min before heating to 50 C. After 4 h, the mixture was concentrated and purified by column chromatography (EtOAc/1/1) to give a white solid, which was treated with saturated NH3 in dioxane (3 mL) in sealed tube at 110 C. overnight. The reaction mixture was concentrated and purified by reverse phase HPLC (MeCN/H2O/0.1% TFA) and lyophilized to give a white powder 4-amino-6-((S)-1-(7-fluoro-2-(pyridin-2-yl)quinolin-3-yl)ethylamino)pyrimidine-5-carbonitrile (19 mg, 15%). 1H NMR (500 MHz, CD3OD) delta ppm 1.78 (d, J=6.85 Hz, 3H) 5.82 (q, J=6.85 Hz, 1H) 7.71 (td, J=8.80, 2.45 Hz, 1H) 7.89 (dd, J=9.66, 2.32 Hz, 1H) 8.10 (ddd, J=7.83, 5.62, 0.98 Hz, 1H) 8.19 (s, 1H) 8.27 (dd, J=9.05, 5.87 Hz, 1H) 8.45 (d, J=7.83 Hz, 1H) 8.63 (td, J=7.95, 1.47 Hz, 1H) 8.94 (s, 1H) 9.03-9.09 (m, 1H). Mass Spectrum (ESI) m/e=386 (M+1).
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Reference:
Patent; Amgen Inc.; Bui, Minna; Cushing, Timothy David; Gonzalez Lopez De Turiso, Felix; Hao, Xiaolin; Lucas, Brian; US2013/267524; (2013); A1;,
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