5-CYANOPYRIMIDINE

Pale Yellow Solid

Pyrimidine-5-carbonitrile (SO3-067): To a suspension of pyrimidine-5-carboxamide (SOS- OSS) (262 mg, 2.12 mmol) and triethyl amine (481 mg, 4.24 mmol) in anhydrous dichoromethane (15 ml) was slowly added a solutionf of trifuoroacetic anhydride (0.36 ml in 4 ml dichloromethane) at 0°C. The reaction mixture was stirred at 0°C to RT for 2 h. and quenched with water (2ml) and washed with NaOH (1 N, 5 ml) and brine (2 x 5 ml). Organic solvent was dried (MgS0In an autoclave, 1 equiv. of aryl halide or heteroaryl halide, 2 equiv. of 1-alkylimidazole, 0.1 equiv. of CuI, 0.2 equiv. of dried K4[Fe(CN)6] (potassium hexacyanoferrate(II)), tetradecane as an internal standard for the GC analysis and a suitable amount of toluene were combined under argon and heated to 160 C. (The K4[Fe(CN)6] was dried by heating powdered K4[Fe(CN)6]x3H2O in a vacuum of 1 mbar to 80 C. for at least 24 hours.) After 16 hours, the reaction mixture was cooled to room temperature. Conversion and yield were determinable by means of gas chromatography. An isolation of the product took place according to the customary workup (distillation, crystallization or chromatography).In an autoclave, 1 equiv. of aryl halide or heteroaryl halide, 2 equiv. of 1-alkylimidazole, 0.1 equiv. of CuI, 0.2 equiv. of dried K4[Fe(CN)6] (potassium hexacyanoferrate(II)), tetradecane as an internal standard for the GC analysis and a suitable amount of toluene were combined under argon and heated to 160 C. (The K4[Fe(CN)6] was dried by heating powdered K4[Fe(CN)6]x3H2O in a vacuum of 1 mbar to 80 C. for at least 24 hours.) After 16 hours, the reaction mixture was cooled to room temperature. Conversion and yield were determinable by means of gas chromatography. An isolation of the product took place according to the customary workup (distillation, crystallization or chromatography).General procedure: Under argon protection, NiCl2·6H2O (0.05mmo 1, 11.9mg), dppf (0.06mmol, 33.3mg), Ζn (0·2mmol, 13.0mg), DMAP (1.0mmol, 122.2mg), Ζn(CN)2 (0.8mmol) , 93.9mg), p-Chloroanisole (1.0 mmol, 140.6 mg) and acetonitrile (5.0 mL) were sequentially added in a 25.0 mL sealed tube, then directly put it into the oil bath at 60 °C, and heating was stopped after 6h, and cooled to room temperature, the reaction solution was directly filtered through a short silica gel column, washed with dichloromethane, concentrated and purified by silica gel column chromatography( given that the product is most easily pulled out, in order to avoid loss of sample mix, unless otherwise noted, both are wet method). Eluent: petroleum ether / ethyl acetate = 20:1, the product was 117.2 mg as a white solid, yield 88percent, and 1H NMR purity was greater than 98percent.Into a 250ml three-necked flask, add a magnetic stirrer and protect it with nitrogen.Then add 1.65 ml (2.0 mol / L) of dimethylamine and 50 ml of anhydrous ether, and slowly add 2.06 ml (1.6 mol / L) of butyl lithium at room temperature.The reaction liquid changed from clear to white turbid liquid. After stirring at room temperature for 20 minutes, Quickly add 0.55 g of p-bromobenzonitrile as a solid. After the reaction is continued for 1 hour, 0.66 g of m-bromopyrimidine is added quickly.After the reaction was continued for 4 hours under the protection of nitrogen, the nitrogen protection was removed. After the reaction was continued for 1 hour under the air atmosphere, Filter under reduced pressure, wash the filter cake with diethyl ether, recrystallize the filter plate with ethanol: water (1: 2), The product was filtered and dried under vacuum. The product was directly reacted without further purification.General procedure: Under argon protection, NiCl2·6H2O (0.05mmo 1, 11.9mg), dppf (0.06mmol, 33.3mg), Zetan (0·2mmol, 13.0mg), DMAP (1.0mmol, 122.2mg), Zetan(CN)2 (0.8mmol) , 93.9mg), p-Chloroanisole (1.0 mmol, 140.6 mg) and acetonitrile (5.0 mL) were sequentially added in a 25.0 mL sealed tube, then directly put it into the oil bath at 60 C, and heating was stopped after 6h, and cooled to room temperature, the reaction solution was directly filtered through a short silica gel column, washed with dichloromethane, concentrated and purified by silica gel column chromatography( given that the product is most easily pulled out, in order to avoid loss of sample mix, unless otherwise noted, both are wet method). Eluent: petroleum ether / ethyl acetate = 20:1, the product was 117.2 mg as a white solid, yield 88%, and 1H NMR purity was greater than 98%.

Molecular Weight:105.10
XLogP3:-0.1
Hydrogen Bond Acceptor Count:3
Exact Mass:105.032697108
Monoisotopic Mass:105.032697108
Topological Polar Surface Area:49.6
Heavy Atom Count:8
Complexity:106
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes