2,4-Dichloro-5-nitropyrimidine

Yellow Solid

5-nitro-uracil (6.28 g, 0.040 mol) was mixed with phosphorus oxychloride (26 ml) and slowly added with stirringN, N-dimethylaniline (8 ml) and then heated to 110 ° C for 8 h. After the reaction, the excess phosphorus oxychloride was distilled off, And the mixture was triturated and chromatographed on silica gel and concentrated to give 6.2 g of a yellow oily liquid. (Yield: 94percent)Compounds Made by Route 1Example 1.1 7-Methoxy-3-phenyl-pyrimido[5, 4-e][l, 2, 4]triazineStep A: 2, 4-Dichloro-5-nitropyrimidineFollowing the procedure in Route 1, a mixture of 5-nitrouracil (5.0 g, 31.8 mmol), phosphoryl chloride (25.0 ml, 274 mmol) and dimethylaniline (6 ml, 47.8 mmol) was heated with occasional shaking, until the reaction commenced. When this had subsided the mixture was refluxed for 2 h, then cooled, and most of the phosphoryl chloride evaporated off under reduced pressure. The residue was poured on ice with vigorous stirring and, after 5 minutes, extracted with ether, the extract was washed with water and dried with NaN, N-dimethylaniline (12.1 mL, 95.5 mmol) is combined with 5-nitrouracil (10.0 g, 63.7 mmol) and stirred under a N5-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): δ 9.16 (1H, s) ppm; 13C NMR (125 MHz, CDCl3): δ 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).25 gm of 5-nitro uracil is suspended in 490 ml of phosphorous oxychloride for 10 minutes and diisopropyl ethylamine is slowly added to the suspension at room temp. The reaction suspension is refluxed at 130

Intermediate in a solid-phase synthesis of diaminopurines.1

Molecular Weight:193.97
XLogP3:2
Hydrogen Bond Acceptor Count:4
Exact Mass:192.9445817
Monoisotopic Mass:192.9445817
Topological Polar Surface Area:71.6
Heavy Atom Count:11
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes