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With sodium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 5h;
0.60g (0.015 mol) of sodium hydroxide was added to a solution of 1.22g(0.0075 mol) of 3,5-dichloropyridin-4-amine in 40 mL of DMF, followed by addition of 2g (0.0075 mol) of <strong>[1897-41-2]2,3,5,6-<strong>[1897-41-2]tetrachloroterephthalonitrile</strong></strong> under stirring,the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatographymonitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phasewas washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentratedunder reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling pointrange 60-90°C) = 1:3, as an eluent) to give 2.16 g of compound C-124 as yellow solid, m.p. 202-204°C.[0132] 1H-NMR (300MHz, internal standard TMS, solvent CDCl3) delta(ppm): 7.28(br, 1H, NH), 8.30(s, 2H, Py-2,6-2H).
2.16 g
With sodium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 5h;
0.60 g (0.015 mol) of sodium hydroxide was added to a solution of 1.22 g (0.0075 mol) of 3,5-dichloropyridin-4-amine in 40 mL of DMF, followed by addition of 2 g (0.0075 mol) of <strong>[1897-41-2]2,3,5,6-<strong>[1897-41-2]tetrachloroterephthalonitrile</strong></strong> under stirring, the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to give 2.16 g of compound C-124 as yellow solid, m.p. 202-204° C. [0197] 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) delta (ppm): 7.28 (br, 1H, NH), 8.30 (s, 2H, Py-2,6-2H).
N-(3,5-dichloropyridin-4-yl)-4-methoxy-2-(methylthio)pyrimidine-5-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75.06%
To a stirred solution of 426 <strong>[84332-06-9]4-methoxy-2-(methylthio)pyrimidine-5-carboxylic acid</strong> (1.7 g, 8.491 mmol, 1.0 eq), in 82 CH2Cl2 (50 mL) was added 429 (COCl)2 (1.45 mL, 16.982 mmol, 2.0 eq) and 47 DMF (0.01 mL) at 0 C. The resulting mixture was stirred at rt for 5 h. The reaction mixture was concentrated, dissolved in CH2Cl2 (5.0 mL) and added to a stirred solution of 430 3,5-dichloropyridin-4-amine (1.385 g, 8.491 mmol, 1.0 eq) and 431 NaH (680 mg, 16.982 mmol, 2.0 eq) in DMF (30 mL) at 0 C. The resulting mixture was stirred at rt for 2 h. The progress of reaction was monitored by LCMS. The reaction mixture was poured in ice cold 7 water (50 mL), extracted with EtOAc (2×100 mL), the combined organic layers were washed with water (50 mL), with brine (50 mL), dried over Na2SO4 concentrated and purified by flash chromatography [silica gel 100-200 mesh elution 0-30% 19 EtOAc in 20 hexane] to afford the desired compound 432 N-(3,5-dichloropyridin-4-yl)-4-methoxy-2-(methylthio)pyrimidine-5-carboxamide (2.2 g, 75.06%) as off white solid. (0500) LCMS: 344.9[M+1]+
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