A kind of method that copper salt catalyzes the synthesis of many substituted pyrimidines
A polysubstituted and pyrimidine technology, applied in the field of copper salt catalyzed synthesis of polysubstituted pyrimidines, can solve the problems of low yield, difficult preparation, complex synthesis steps, etc., and achieves the effects of high efficiency, wide substrate adaptability and wide application range.
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Embodiment 1
[0057] The synthesis of 2,4,6-triphenylpyrimidine comprises the following steps:
[0058] A. Mix 0.3mmol benzamidine hydrochloride with 0.39mmol benzyl alcohol and 0.45mmol 1-phenylethanol, then add 0.03mmol Cu(OAC) to it 2 , 0.9 mmol Na 2 CO 3 and 3mL of toluene, stirred and reacted at 120°C for 24 hours;
[0059] B. The resulting product was extracted with ethyl acetate, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography with petroleum ether: ethyl acetate = 50:1 as the eluent to obtain white The solid, 2,4,6-triphenylpyrimidine, yielded 84% and had a melting point of 184-186°C.
[0060] Its hydrogen spectrum and carbon spectrum NMR are as follows: figure 2 , image 3 As shown, the NMR characterization data are as follows:
[0061] 1 H NMR (300MHz, CDCl 3 )δ8.69–8.67 (m, 2H), 8.25-8.24 (m, 4H), 7.97 (s, 1H), 7.50-7.48 (m, 9H).
[0062] 13 C NMR (75MH...
Embodiment 2
[0064] 2, the synthesis of 4-bisphenyl-6-p-methylphenylpyrimidine comprises the following steps:
[0065] A, 0.3mmol p-benzamidine hydrochloride and 0.39mmol p-methyl benzyl alcohol, 0.45mmol 1-phenylethanol, then add 0.03mmol Cu(OAc) 2 , 0.9mmol KOH and 3mL toluene, stirred and reacted at 120°C for 24 hours, the product was obtained;
[0066] B. Extract the product with ethyl acetate, dry it to obtain a crude product, and purify the crude product with silica gel column chromatography using petroleum ether: ethyl acetate = 50:1 as the eluent to obtain a white solid 2,4-bisphenyl -6-p-methylphenylpyrimidine. Yield 83%, 150-152°C.
[0067] Its hydrogen spectrum and carbon spectrum NMR are as follows: Figure 4 , Figure 5 As shown, the NMR characterization data are as follows:
[0068] 1 H NMR (300MHz, CDCl 3 )δ8.67(d, J=5.7Hz, 2H), 8.24(d, J=4.8Hz, 2H), 8.15(d, J=7.8Hz, 2H), 7.95(s, 1H), 7.50-7.48( m, 6H), 7.32 (d, J = 7.5Hz, 2H);
[0069] 13 C NMR (75MHz, CDCl 3 )δ1...
Embodiment 3
[0071] The synthesis of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine comprises the following steps:
[0072] A. Take 0.3mmol benzamidine hydrochloride, 0.39mmol p-chlorobenzyl alcohol, 0.40mmol 1-phenylethanol, and then add 0.03mmol Cu(OAc) 2 , 0.9mmol KOH and 2.5mL toluene, stirred and reacted at 120°C for 24 hours;
[0073] B. The product is extracted with ethyl acetate, dried to obtain a crude product, and the crude product is purified by silica gel column chromatography (solvent volume ratio is petroleum ether:ethyl acetate=50:1) to obtain a white solid that is 4-(4- Chlorophenyl)-2,6-diphenylpyrimidine, the yield is 84%, and the melting point is 164°C.
[0074] Its hydrogen spectrum and carbon spectrum NMR are as follows: Figure 6 , Figure 7 As shown, the NMR characterization data are as follows:
[0075] 1 H NMR (300MHz, CDCl 3 )δ8.67 (d, J=7.5Hz, 2H), 8.24-8.18 (m, 4H), 7.92 (s, 1H), 7.50-7.47 (m, 8H);
[0076] 13 C NMR (75MHz, CDCl 3 )δ164.89, 164.50, 163.42, 1...
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