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. 38275-55-7, name is 5-Fluoropyrimidine-2-carbonitrile. A new synthetic method of this compound is introduced below., Computed Properties of C5H2FN3
To a mixture of 1-ethyl-7-fluoro-6-methoxy-1,2,3,4-tetrahydroisoquinoline (0.3 g, 1.43 mmol) and 5-fluoropyrimidine-2-carbonitrile (0.26 g, 2.15 mmol) in DMF (8 mL) was added cesium carbonate (1.4 g, 4.3 mmol) under N2. The mixture was stirred at 100 C for 12 hours. The reaction mixture was cooled to rt, diluted with H2O (30 mL) and extracted with EtOAc (3 x 30 mL). The combined organic phase was washed with saturated aqueous brine solution (30 mL), dried over anhydrous sulfate, filtered and concentrated in vacuum. The residue was purified via normal phase SiO2 chromatography (0-20% EtOAc/petroleum ether) to give 5-(1-ethyl-7-fluoro-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl) pyrimidine-2- carbonitrile as a yellow solid (0.2 g, 45% yield, m/z: 313 [M+H]+ observed). 1H NMR (400 MHz, CDCl3) d 8.31 (s, 2H), 6.89 (d, J = 10.8 Hz, 1H), 6.80 (d, J = 8 Hz, 1H), 4.54 (t, J = 7.6 Hz, 1H), 3.90 (s, 3H), 3.73-3.67 (m, 1H), 3.61-3.54 (m, 1H), 3.03 (t, J = 6 Hz, 2H), 2.00-1.93 (m, 1H), 1.81-1.74 (m, 1H), 1.01 (t, J = 7.6 Hz, 3H).
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Reference:
Patent; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; COLE, Andrew G.; DORSEY, Bruce D.; DUGAN, Benjamin J.; FAN, Yi; GOTCHEV, Dimitar B.; KAKARLA, Ramesh; QUINTERO, Jorge; SOFIA, Michael J.; (220 pag.)WO2019/222238; (2019); A2;,
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