Related Products of 611-08-5 ,Some common heterocyclic compound, 611-08-5, molecular formula is C4H3N3O4, 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.
5-nitropyrimidine-2,4(1H,3H)-dione 5 (8.66 g, 55.1 mmol) was dissolved in freshly distilled phosphorus oxytrichloride (25.7 mL, 275.5 mmol) at room temperature. N,N-Dimethylaniline (17.4 mL, 137.8 mmol) was added dropwise to the stirred solution and the reaction was refluxed for 3 hours, or until complete. The black solution was cooled and concentrated under reduced pressure to remove excess phosphorus oxytrichloride, then poured into ice-water (82 mL). The aqueous solution was extracted with diethyl ether (3 x 110 mL), and the combined organic layers were washed with brine (160 mL), dried over anhydrous magnesium sulfate and the solvent evaporated to yield a brown oil. The crude product was purified by silica gel chromatography using ethyl acetate/hexane (1/10 v/v) as an eluent. The product was obtained as a yellow oil 5 (4.3 g, 22.5 mmol, 41percent). m.p. 29-30 °C; Rf 0.42 (1/10 v/v ethyl acetate/hexane); IR (ZnSe cell, solid) vmax: 1541 (s, NO2), 1342 (s, NO2/C-N=C), 1305 (s, NO2/C-N=C), 1203 (s, C-Cl), 1178 (s, C-Cl), 871 (s, C=C-H), 678 (s, C=C-H); 1H NMR (500 MHz, CDCl3): delta 9.16 (1H, s) ppm; 13C NMR (125 MHz, CDCl3): delta 162.74 (4-CCl), 156.62 (6-CH), 155.69 (2-CCl), 141.67 (5-CNO2) ppm; LRMS (+ GC/MS, 3.14 min) m/z: 197, 195, 193 ([M]+, 7, 39, 59percent), 160, 158 ([M – Cl]+, 25, 70percent), 137, 135 ([M – (CH2ClN)2 + H]+, 34, 53percent), 124, 122, 120 ([M ? (C2HClN)3 + H]+, 11, 65, 100percent), 93 (63percent), 65, 63 (32, 78percent).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 611-08-5, 5-Nitrouracil, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Munoz, Lenka; Kavanagh, Madeline E.; Phoa, Athena F.; Heng, Benjamin; Dzamko, Nicolas; Chen, Ew-Jun; Doddareddy, Munikumar Reddy; Guillemin, Gilles J.; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 29 – 34;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia