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Synthesis method and application of 2, 4-fluoro-pyrrole [1, 2] pyrimidine-7-formonitrile
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A synthesis method and pyrrole technology are applied in the fields of drug combination, cardiovascular system diseases, organic chemistry, etc., which can solve the problems of cumbersome post-processing operations, many reaction by-products, and low product purity, and achieve easy post-processing and purification. Mild conditions and the effect of reducing production steps
Pending Publication Date: 2021-08-27
安徽珐诺伊医药科技有限公司
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[0006] Aiming at the deficiencies of the prior art, the present invention provides a synthetic method of 2,4-fluoro-pyrrole [1,2] pyrimidine-7 carbonitrile, based on the development of a brand-new synthetic method to solve the drug of cardiovascular disorders In the preparation method of intermediate synthetic compounds, there are many reaction by-products, low conversion rate, cumbersome post-processing operations, and low product purity. A new general-purpose, economical, efficient, and green synthetic method is developed to achieve easy availability of raw materials and low price. Inexpensive, simple operation, and less pollution product synthesis principle, the final preparation yield can reach more than 8%
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Embodiment 1
[0027] A kind of synthetic method of 2,4 fluoro-pyrrole [1,2] pyrimidine-7 carbonitrile, reaction formula is as shown in formula (I):
[0028]
[0029] Include the following steps:
[0030] Step 1: Synthesis of Compound 3
[0031] CuI (7.2 g, 39 mmol) was added to a mixture of compound 1 (36 g, 126.5 mmol) and Pd(PPh3)4 (7.3 g, 6.5 mmol) in toluene (240 mL) at room temperature under nitrogen. Then, compound 2 (18.6 mL, 126.5 mmol), Et3N (58.5 mL, 405 mmol) and TBAF (126.5 mL, 126.5 mmol, 1M in THF) were added, and the mixture was stirred at the same temperature for 17 h. After the reaction was complete, the mixture was filtered and the filtrate was evaporated under vacuum. The residue was purified by recrystallization from a mixed solvent of petroleumether / ethyl acetate (about 10:1 by volume) to obtain compound 3 as a white solid (29.8 g, 85% yield). 1H NMR(400MHz,CDCl3): δ2.08(s,3H),8.70(s,2H).EI-MS:196,169,117,104,90,64,52.m.p.: 98-100℃.
[0032] Step 2: Synthesis of...
Embodiment 2
[0039] A kind of synthetic method of 2,4 fluoro-pyrrole [1,2] pyrimidine-7 carbonitrile, reaction formula is as shown in formula (I):
[0040]
[0041] Include the following steps:
[0042] Step 1: Synthesis of Compound 3
[0043] CuI (4.8 g, 25.3 mmol) was added to a mixture of compound 1 (24 g, 84.3 mmol) and Pd(PPh3)4 (4.87 g, 4.3 mmol) in toluene (160 mL) at room temperature under nitrogen. Then, compound 2 (12.4 mL, 84.3 mmol), Et3N (39 mL, 270 mmol) and TBAF (84.3 mL, 84.3 mmol, 1M in THF) were added, and the mixture was stirred at the same temperature for 17 h. After the reaction was complete, the mixture was filtered and the filtrate was evaporated under vacuum. The residue was purified by recrystallization from a mixed solvent of petroleumether / ethyl acetate (about 10:1 by volume) to obtain compound 3 as a white solid (33.53 g, 90% yield). 1H NMR(400MHz, CDCl3):δ2.08(s,3H),8.70(s,2H).EI-MS:196,169,117,104,90,64,52. m.p.:98-100℃.
[0044] Step 2: Synthesis of c...
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Abstract
The invention belongs to the technical field of synthesis of drug intermediates, particularly relates to a synthesis method and application of 2, 4-fluoro-pyrrole [1, 2] pyrimidine-7-formonitrile, provides the synthesis method of the 2, 4-fluoro-pyrrole [1, 2] pyrimidine-7-formonitrile, and aims at developing a brand new synthesis method to solve the defects of more reaction byproducts, low conversion rate, complicated post-treatment operation, low product purity and the like in a preparation method of an intermediate synthetic compound of a medicine for treating cardiovascular disorders; and a novel, universal, economical, efficient and environment-friendly synthetic method is developed, so that the product synthesis principles of easily available raw materials, low price, simple operation and less pollution are achieved, and the final preparation yield reaches 8% or above.
Description
technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, in particular to a synthesis method and application of 2,4-fluoro-pyrrole[1,2]pyrimidine-7carbonitrile. Background technique [0002] The present invention relates to novel active ingredient combinations consisting of other known active ingredients, known as pyridine-3-carbonitrile processes, said compounds being used as intermediate synthetic compounds for the production of medicaments, in particular for Synthetic compounds intermediates in the production of drugs for the treatment and / or prevention of cardiovascular disorders. [0003] CN201180042458.8 describes a process for the preparation of 5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile, which is used in the synthesis of intermediate compounds for pharmaceuticals, in particular for the production of Synthetic compounds intermediates of drugs for the treatment and / or prevention of cardiovascular disorde...
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