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Synthetic process of 7‑bromo‑4‑chlorothieno[3,2‑d]pyrimidine

A synthesis process, a technology for chlorothiophene, applied in directions such as organic chemistry, can solve problems such as unfavorable large-scale application, low yield, affecting total yield, etc., and achieve the effects of increasing individual yields, increasing total yields, and reducing costs

Active Publication Date: 2017-09-29
上海泰坦科技股份有限公司
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Problems solved by technology

[0005] Although the above-mentioned prior art discloses a synthesis method of 7-bromo-4-chlorothieno[3,2-D]pyrimidine, which can meet certain needs, but in the process of realizing the present invention, the inventors found that the above-mentioned present There are still some deficiencies and shortcomings in the technical solution, such as in the second step, the yield of upper bromine is 76%, which is low and affects the total yield, which is not conducive to large-scale industrial application

Method used

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  • Synthetic process of 7‑bromo‑4‑chlorothieno[3,2‑d]pyrimidine

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Embodiment 1

[0019] This embodiment relates to a synthesis process of 7-bromo-4-chlorothieno[3,2-D]pyrimidine, which consists of the following steps:

[0020] Step 1, the 3-amino-2-formic acid methyl thiophene and 1.2mol formamide of 1mol are joined in the solvent ethylene glycol methyl ether, the mol ratio of 3-amino-2-formic acid methyl thiophene and formamide is 1: 1.2, heat to reflux at 130°C for 3 hours, then add 50ml of saturated saline when the solvent is no longer reduced, filter, and dry at 40°C to obtain solid 4-hydroxythienopyrimidine with a yield of 92% and a purity of 99.2%;

[0021] Step 2, the above-mentioned 4-hydroxythienopyrimidine and N-bromosuccinimide (NBS), sodium hexametaphosphate are added in the solvent acetone, 4-hydroxythienopyrimidine, N-bromosuccinimide , The molar ratio of sodium hexametaphosphate is 1:1:0.06, after reacting at 15°C for 4h, filter, discard the solid, add 50ml of water to the filtrate, stir, filter, collect the solid, and dry at 40°C to obtain ...

Embodiment 2

[0025] This embodiment relates to a synthesis process of 7-bromo-4-chlorothieno[3,2-D]pyrimidine, which consists of the following steps:

[0026] Step 1, the 3-amino-2-formic acid methyl thiophene and 1.2mol formamide of 1mol are joined in the solvent ethylene glycol methyl ether, the mol ratio of 3-amino-2-formic acid methyl thiophene and formamide is 1: 1.2, heat to reflux at 120°C for 4 hours, then add 50ml of saturated saline when the solvent is no longer reduced, filter, and dry at 40°C to obtain solid 4-hydroxythienopyrimidine, 93%, purity 99.3%;

[0027] Step 2, the above-mentioned 4-hydroxythienopyrimidine, N-bromosuccinimide (NBS), sodium hexametaphosphate are added in the solvent acetone, 4-hydroxythienopyrimidine, N-bromosuccinimide , The molar ratio of sodium hexametaphosphate is 1:1.5:0.03, after reacting at 20°C for 9h, filter, discard the solid, add 50ml of water to the filtrate, stir, filter, collect the solid, and dry at 40°C to obtain 4-hydroxy-7- Bromothien...

Embodiment 3

[0031] This embodiment relates to a synthesis process of 7-bromo-4-chlorothieno[3,2-D]pyrimidine, which consists of the following steps:

[0032] Step 1, the 3-amino-2-formic acid methyl thiophene and 1.2mol formamide of 1mol are joined in the solvent ethylene glycol methyl ether, the mol ratio of 3-amino-2-formic acid methyl thiophene and formamide is 1: 1.2, heat to reflux at 130°C for 6 hours, then add 50ml of saturated saline when the solvent is no longer reduced, filter, and dry at 40°C to obtain solid 4-hydroxythienopyrimidine, 92.5%, purity 99.1%;

[0033] Step 2, the above-mentioned 4-hydroxythienopyrimidine, N-bromosuccinimide (NBS), sodium hexametaphosphate are added in the solvent acetone, 4-hydroxythienopyrimidine, N-bromosuccinimide , The molar ratio of sodium hexametaphosphate is 1:1:0.1, after reacting at 30°C for 1h, filter, discard the solid, add 50ml of water to the filtrate, stir, filter, collect the solid, and dry at 40°C to obtain 4-hydroxy-7- Bromothieno...

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Abstract

The invention relates to a synthetic method of 7-bromo-4-chlorothieno [3,2-D] pyrimidine. The synthetic method comprises the following steps: adding 3-amino-2-methyl formate thiophene and formamide into ethylene glycol monomethyl ether, heating to 120-140 DEG C to reflux, then adding saturated salt water when a solvent is not reduced anymore, and filtering to obtain solid 4-hydroxyl thieno-pyrimidine; adding 4-hydroxyl thieno-pyrimidine, N-bromo-succinimide and sodium hexametahposphate into acetone, reacting at 5-30 DEG C, filtering, adding water into a filtrate, stirring, filtering, and collecting solids to obtain 4-hydroxyl-7-bromo-thieno-pyrimidine; and adding the 4-hydroxyl-7-bromo-thieno-pyrimidine into phosphorus oxychloride, heating to reflux, then pouring into ice water, stirring until solids are generated, filtering, and drying in the air to obtain 7-bromo-4-chlorothieno [3,2-D] pyrimidine. By use of the synthetic process, the total yield of the 7-bromo-4-chlorothieno [3,2-D] pyrimidine is improved, the cost is effectively reduced. The synthetic method of 7-bromo-4-chlorothieno [3,2-D] pyrimidine is suitable for industrial large-scale synthesis application.

Description

technical field [0001] The invention relates to a synthesis process of thienopyrimidine compounds, in particular to a synthesis process of 7-bromo-4-chlorothieno[3,2-D]pyrimidine. Background technique [0002] Thienopyrimidine heterocyclic compounds have bactericidal, herbicidal, insecticidal and medicinal activities, and have broad application prospects, especially thienopyrimidines are a new type of anti-tumor drugs that inhibit SRC family protein kinases. The synthesis of an important intermediate 7-bromo-4-chlorothieno[3,2-D]pyrimidine (namely: 7-bromo-4-chlorothieno[3,2-D]pyrimidine, CAS No. : 31169-27-4), so it is of great significance and application value to study the synthetic method and process improvement of this intermediate. The structural formula of 7-bromo-4-chlorothieno[3,2-D]pyrimidine is shown below. [0003] [0004] CN102250111A (published date 2011.11.23) discloses a preparation method of 7-bromo-4-chlorothienopyrimidine, using 3-aminothiophene-2-ca...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 谢应波张庆张华徐肖冰罗桂云
Owner 上海泰坦科技股份有限公司
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