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Synthetic method of OLED material intermediate benzoyl pyrimidine compound

A technology of benzoylpyrimidine and synthesis method, which is applied in the field of synthesis of benzoylpyrimidine compounds as intermediates of OLED materials, and can solve the problems of expensive phenylboronic acid and high production cost

Active Publication Date: 2018-06-12
棓诺(苏州)新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] This method also has only one-step reaction, but sulfonic acid phenol ester often needs to be synthesized by itself, and the raw material phenylboronic acid is relatively expensive, and also needs to be catalyzed by a catalyst containing precious metal palladium, so the production cost of this method is still high

Method used

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  • Synthetic method of OLED material intermediate benzoyl pyrimidine compound
  • Synthetic method of OLED material intermediate benzoyl pyrimidine compound
  • Synthetic method of OLED material intermediate benzoyl pyrimidine compound

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Effect test

Embodiment 1

[0084] The synthesis of embodiment 1,5-benzoyl-2-hydroxypyrimidine

[0085] (1) In a 250ml three-necked flask, add 12g (0.174mol) of sodium ethoxide and 100mL of anhydrous toluene, stir, add dropwise (30 minutes) 20.5g (0.17mol) of acetophenone and 25.5g (0.174mol) of acetophenone The uniformly mixed solution of diethyl oxalate was heated to 50-60°C after dropping, and stirred for 4 hours. Cool to room temperature, wash with 5% dilute hydrochloric acid solution until the pH value of the eluent is 5-6, separate the liquids, collect the toluene layer (located on the upper layer), dry with anhydrous sodium sulfate for 30 minutes, filter, and the filtrate water pump reduces Toluene was recovered by pressure distillation, and the residue was recrystallized with 300ml of 95% ethanol to obtain 32.6g of pure ethyl ester intermediate I (purity: 99.0%), yield 87%, Mp.67-68°C.

[0086] (2) In a 25ml single-necked flask, add 2.8g (0.0125mol) of ethyl ester intermediate I, 4mL (0.025mol) ...

Embodiment 2

[0090] The synthesis of embodiment 2,5-benzoyl-2-hydroxypyrimidine

[0091] (1) In a 250ml three-necked flask, add 9.5g (0.174mol) of sodium methoxide and 100mL of dry xylene, stir, add dropwise (30 minutes) 20.5g (0.17mol) of acetophenone and 20.6g (0.174mol) of acetophenone ) a homogeneously mixed solution of dimethyl oxalate, the temperature was raised to 40-50° C. after dropping, and the reaction was stirred for 4 hours. Cool to room temperature, wash with 5% dilute hydrochloric acid solution, and adjust the pH value to 5-6, separate the layers, collect the xylene layer, dry it with anhydrous sodium sulfate for 30 minutes, filter, and recover the xylene by distilling the filtrate under reduced pressure with a water pump. The residue was recrystallized with 95% ethanol to obtain 30.2 g of the pure methyl ester intermediate I (purity: 98.9%), with a yield of 86%.

[0092] (2) In a 50ml single-necked flask, add 5.16g (0.025mol) of methyl ester intermediate I, 6mL (0.05mol) o...

Embodiment 3

[0096] The synthesis of embodiment 3,5-benzoyl-2-hydroxypyrimidine

[0097] (1) In a 250ml three-necked flask, add 25.5g (0.265mol) of sodium tert-butoxide and 100mL of dry cyclohexane, stir, add dropwise (30 minutes) 20.5g (0.17mol) of acetophenone and 51.0g (0.348mol) a homogeneously mixed solution of diethyl oxalate, the temperature was raised to 70-80°C after dropping, and the reaction was stirred for 4 hours. Cool to room temperature, wash with 5% dilute hydrochloric acid solution, and adjust the pH value to 5-6, separate the liquid, collect the cyclohexane layer, dry with anhydrous sodium sulfate for 30 minutes, filter, and the filtrate is distilled under reduced pressure by a water pump to recover the cyclohexane alkane, and the residue was recrystallized with 95% ethanol to obtain 30.8 g of the pure ethyl ester intermediate I (purity: 98.7%), with a yield of 82%.

[0098] (2) In a 50ml single-necked flask, add 5.6g (0.025mol) of ethyl ester intermediate I, 24mL (0.15m...

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Abstract

The invention discloses a synthetic method of an OLED material intermediate benzoyl pyrimidine compound. The synthetic method comprises the following steps: mixing alkali, a solvent I as well as substituent acetophenone and oxalic acid diester which are used as raw materials, and then performing reaction, thus obtaining an intermediate I; mixing the intermediate I, a solvent II as well as a diamine compound and orthoformate trimester which are used as raw materials, and then performing reaction, thus obtaining an intermediate II; mixing the intermediate II, ethanol and acetic acid, and then performing reaction, thus obtaining an intermediate III; mixing the intermediate III and an ethanol aqueous solution, adding alkali, and then performing reaction, thus obtaining an intermediate IV; mixing the intermediate IV and a solvent III, and reacting, thus obtaining the benzoyl pyrimidine compound as a target product. The synthetic method of the benzoyl pyrimidine compound adopts the raw materials which are cheap and easy to obtain to synthesize the benzoyl pyrimidine compound under simple and mild conditions.

Description

technical field [0001] The invention belongs to the field of chemistry, in particular to a method for synthesizing OLED material intermediates, benzoylpyrimidine compounds. Background technique [0002] The pyrimidine ring is a common six-membered conjugated heterocycle. Compared with the benzene ring and the pyridine ring, the pyrimidine ring is more electron-deficient due to the electron-withdrawing effect of the two nitrogen atoms, and has a stronger ability to accept electrons. Therefore, it is more suitable for as the electron transport unit. The pyrimidine unit also has a certain basicity. As a potential ligand unit, it plays a very important role in modifying and regulating the photoelectric properties of the molecule. The introduction of the pyrimidine ring can significantly improve the luminescence performance of the material. Therefore, pyrimidine derivatives are widely used in OLED functional materials, OFET materials, liquid crystal materials, and even fluoresce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/34C07D239/38C07D239/42C07D239/26
CPCC07D239/26C07D239/34C07D239/38C07D239/42
Inventor 吴清来
Owner 棓诺(苏州)新材料有限公司
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