Method for preparing biphenyl substituted pyrimidine compounds
A compound and complex technology, which is applied in the field of preparation of pyrimidine derivatives, can solve the problems of increased product groups, reduced solubility, reduced oxidation and hydrogenation yields, and achieves high product yields, low preparation costs, and easy steps concise effect
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Embodiment 1
[0033] Coupling reaction of 2-chloro-5-ethylpyrimidine with biphenylboronic acid:
[0034] Under argon protection, in a 50ml Schlenk bottle, add 931mg (3.5mmol) K successively 3 PO 4 ·3H 2 O, 6.74 mg (0.03 mmol) palladium acetate, 30.6 mg (0.06 mmol) saturated n-propyl aryl imidazolium salt and 5 ml tetrahydrofuran, stirred at room temperature for 10 minutes. Then 236mg (1.2mmol) of biphenylboronic acid, 143mg (1.0mmol) of 2-chloro-5-ethylpyrimidine, 10ml of tetrahydrofuran and 3ml of water were added, and the reactant was heated to reflux for 10 hours and stopped. Cool the reaction solution, remove most of the organic solvent under reduced pressure with a water pump, then add 10 mL of water to dilute, extract with ethyl acetate (10 mL×3), combine the organic phases, dry over anhydrous sodium sulfate, and recover the solvent. Separated by column chromatography, 244mg of white solid product was obtained, melting point (m.p.): 92-94°C, yield 94%.
Embodiment 2
[0036]Coupling reaction of 2-chloro-5-propylpyrimidine with biphenylboronic acid:
[0037] Under argon protection, in a 50ml Schlenk bottle, add 931mg (3.5mmol) K successively 3 PO 4 ·3H 2 O, 6.74 mg (0.03 mmol) palladium acetate, 30.6 mg (0.06 mmol) saturated n-propyl aryl imidazolium salt and 5 ml tetrahydrofuran, stirred at room temperature for 10 minutes. Then 236mg (1.2mmol) of biphenylboronic acid, 157mg (1.0mmol) of 2-chloro-5-propylpyrimidine, 10ml of tetrahydrofuran and 3ml of water were added, and the reactant was heated to reflux for 10 hours and stopped. Cool the reaction solution, remove most of the organic solvent under reduced pressure with a water pump, then add 10 mL of water to dilute, extract with ethyl acetate (10 mL×3), combine the organic phases, dry over anhydrous sodium sulfate, and recover the solvent. Separated by column chromatography, 247mg of white solid product was obtained, m.p.: 96-97°C, yield 90%.
Embodiment 3
[0039] Coupling reaction of 2-chloro-5-pentylpyrimidine with biphenylboronic acid:
[0040] Under argon protection, in a 50ml Schlenk bottle, add 931mg (3.5mmol) K successively 3 PO 4 ·3H 2 O, 6.74 mg (0.03 mmol) palladium acetate, 30.6 mg (0.06 mmol) saturated n-propyl aryl imidazolium salt and 5 ml tetrahydrofuran, stirred at room temperature for 10 minutes. Then 236mg (1.2mmol) of biphenylboronic acid, 185mg (1.0mmol) of 2-chloro-5-pentylpyrimidine, 10ml of tetrahydrofuran and 3ml of water were added, and the reactant was heated to reflux for 10 hours and stopped. Cool the reaction solution, remove most of the organic solvent under reduced pressure with a water pump, then add 10 mL of water to dilute, extract with ethyl acetate (10 mL×3), combine the organic phases, dry over anhydrous sodium sulfate, and recover the solvent. It was separated by column chromatography to obtain 296 mg of white solid product, ptt (°C): Cr84N 88Iso. The yield was 98%.
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