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Preparation method of 2, 4-diaminopyrimidine-3-oxide

A technology of diaminopyrimidine and oxide, which is applied in the field of synthesis of 2,4-diaminopyrimidine-3-oxide, and can solve the problem of low yield

Pending Publication Date: 2022-04-12
CHONGQING DONGHUAN SCI & TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the above-mentioned shortcomings such as low yield, the present application has carried out process route improvement, to be suitable for the method of industrial scale-up

Method used

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  • Preparation method of 2, 4-diaminopyrimidine-3-oxide
  • Preparation method of 2, 4-diaminopyrimidine-3-oxide
  • Preparation method of 2, 4-diaminopyrimidine-3-oxide

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Experimental program
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Effect test

Embodiment 1

[0030]

[0031] Put 22.2g (0.2mol) of cytosine, 61.3g (0.4mol, 2eq) of phosphorus oxychloride and 200mL of acetonitrile into the reaction kettle. Raise the temperature to 35°C, add 40.5g (0.4mol, 2eq) of triethylamine dropwise, raise the temperature to 80-82°C and stir for 4 hours after the dropwise addition, take a sample by HPLC to detect that the remaining cytosine of the raw material is less than 0.3%, lower the temperature, and concentrate under reduced pressure to remove For most of the acetonitrile and phosphorus oxychloride, put the reaction solution into 10°C water to quench, adjust the pH to 8-9 with 20% aqueous sodium carbonate solution, add dichloromethane for extraction, concentrate, add n-heptane for beating, and obtain 4- Amino-2-chloropyrimidine 23.2g, yield 89.5%, HPLC 98.9%. 1 HNMR (400MHz, CDCl 3 ):7.80-7.78(m,1H),6.93(s,2H),6.14-6.12(m,1H).

Embodiment 2

[0033]

[0034] 22.2 g (0.2 mol) of isocytosine and 200 mL of toluene were put into the reactor. Raise the temperature to 55°C, add 62.5g (0.3mol, 1.5eq) of phosphorus pentachloride in batches, raise the temperature to 102-108°C and stir for 6 hours, take a sample by HPLC to detect that the remaining cytosine of the raw material is less than 0.2%, cool down and concentrate under reduced pressure to remove most of it Toluene, put the reaction solution into 10°C water to quench, use 20% sodium carbonate aqueous solution to adjust pH=8~9, add dichloromethane to extract, concentrate, add n-heptane for beating, and obtain 2-amino-4-chloropyrimidine 24.1 g, yield 93.1%, HPLC 95.4%. 1 HNMR (400MHz, CDCl 3 ):8.70-8.68(m,1H),6.90-6.88(m,1H),6.33(s,2H).

Embodiment 3

[0036]

[0037] Put 22.4g (0.2mol) of uracil and 153.3g (1.0mol, 5eq) of phosphorus oxychloride into the reactor. Raise the temperature to 105-108°C and stir the reaction for 8 hours, sample HPLC to detect the remaining 0.12% of the raw material cytosine, cool down and concentrate under reduced pressure to remove most of the phosphorus oxychloride, put the reaction solution into 10°C water to quench, and use 10% bicarbonate Potassium aqueous solution was used to adjust the pH to 8-9, dichloromethane was added for extraction, concentrated, and n-heptane was added for slurry to obtain 28.5 g of 2,4-dichloropyrimidine with a yield of 95.7% and HPLC of 99.1%. 1 HNMR (400MHz, CDCl 3 ):8.83-8.80(m,1H),7.38-7.36(m,1H).

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Abstract

The invention discloses a preparation method of 2, 4-diaminopyrimidine-3-oxide, and belongs to the technical field of organic synthesis. Cytosine, isocytosine or uracil is used as a raw material, the raw material and a chlorination reagent are used for carrying out chlorination on hydroxyl, then the raw material and an oxidation reagent are used for carrying out reaction on 3-site N to generate nitrogen oxide, then the nitrogen oxide and ammonia / methanol are subjected to ammonolysis to obtain 2, 4-diaminopyrimidine-3-oxide, the three different raw materials belong to the same synthetic route, the selectivity is high, the operation is simple and convenient, the condition is mild, and the cost is low.

Description

technical field [0001] The invention relates to a synthesis method of 2,4-diaminopyrimidine-3-oxide, which belongs to the technical field of organic synthesis. Background technique [0002] 2,4-diaminopyrimidine-3-oxide, the English name is 2,4-diaminopyrimidine-3-oxide, molecular formula: C4H6N4O, abbreviation: 2,4-DPO, molecular weight: 126.117, CAS: 74638-76-9, 2,4-diaminopyrimidine-3-oxides or their salts have therapeutic effects as active substances in the treatment of collagen maturation or collagen organization disorders, and US5328914A, 1994 also reported that pyrimidine 3-oxide derivatives and their salts have therapeutic effects on hair loss. The best use, the amount is increasing, including the acetate of 2,4-diaminopyrimidine-3-oxide. At the same time, pyrimidine compounds have the advantages of high efficiency, low toxicity, and unique mode of action, so their molecular design, synthesis and biological activity research is still a very active field in the resea...

Claims

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Application Information

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IPC IPC(8): C07D239/48
CPCY02P20/55
Inventor 张克伦陈天豪邓恩元周芝凤张培李小会
Owner CHONGQING DONGHUAN SCI & TECH DEV
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