Category: pyrimidines

Electric Literature of 3680-69-1 ,Some common heterocyclic compound, 3680-69-1, molecular formula is C6H4ClN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2-E, 20.0 g, 130.7 mmol) dissolved in DCM (800 mL) was treated portion-wise with N-bromosuccinimide (26.7 g, 149.8 mmol), while maintaining the temperature around 25-30 C. The reaction mixture was stirred at room temperature overnight. Water was added (500 mL) and the phases were separated. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was triturated in Et2O affording after filtration 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine as a white solid (2-F, 22.43 g, 74%). M.p.: 242-244 C.; NMR (400 MHz, DMSO-d6) delta 12.96 (s, 1H), 8.61 (s, 1H), 7.94 (s, 1H); MS m/z 232 [M(35Cl, 79Br)+H]+, 234 [M(35Cl, 81Br)+H]+, 234 [M(37Cl, 79Br)+H]+, 236 [M(37Cl, 81Br)+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3680-69-1, its application will become more common.

Reference:
Patent; ArQule, Inc.; Lapierre, Jean-Marc; Eathiraj, Sudharshan; Namdev, Nivedita; Schwartz, Brian; Ota, Yusuke; Momose, Takayuki; Tsunemi, Tomoyuki; Inagaki, Hiroaki; Nakayama, Kiyoshi; (18 pag.)US9630968; (2017); B1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.271-70-5, name is 7H-Pyrrolo[2,3-d]pyrimidine, molecular formula is C6H5N3, molecular weight is 119.124, as common compound, the synthetic route is as follows.COA of Formula: C6H5N3

To 7H-pyrrolo[2,3-d]pyrimidine (6, 0.450 g, 3.78 mmol), N-(2,4-difluoro-3-formyl-phenyl)-4-trifluoromethyl-benzenesulfonamide (10, 1.52 g, 4.16 mmol), and potassium hydroxide (0.689 g, 12.3 mmol), 6.6 mL of methanol was added. The solution was allowed to stir at room temperature for 8 hours, then poured into 50 mL of water and 50 mL of aqueous saturated ammonium chloride and extracted 2*50 mL and 1*25 mL with ethyl acetate. The combined organic layers were washed with water and brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluding with a gradient of 0-80% ethyl acetate in hexane (with 4% acetic acid) over 15 minutes. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a white solid (P-0003, 754 mg). 1H-NMR (dmso-d6) consistent with the desired compound. MS (ESI) [M-H+]-=483.4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,271-70-5, 7H-Pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Plexxikon, Inc.; US2009/286783; (2009); A1;,
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Electric Literature of 62802-38-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.62802-38-4, name is 5-Bromo-2-fluoropyrimidine, molecular formula is C4H2BrFN2, molecular weight is 176.9745, as common compound, the synthetic route is as follows.

[00378] 65A: 2-fluoro-5-(2-fluoro-5-methoxyphenyl)pyrimidine. To a stirred solution of 5-bromo-2-fluoropyrimidine (707 mg, 3.99 mmol) in Toluene (5.0 mL) was added (2- fluoro-5-methoxyphenyl)boronic acid (815 mg, 4.79 mmol), tetrakis(triphenylphosphine) palladium(O) (231 mg, 0.200 mmol) and potassium carbonate (1656 mg, 1 1.98 mmol). The resulting mixture was purged with argon and stirred at 1 10 C for 16h. After cooled to room temperature, the reaction mixture was diluted with water and extracted with DCM. The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give a solid which was purified by chromatography to afford 2-fluoro-5- (2-fluoro-5-methoxyphenyl)pyrimidine (265 mg, 1.169 mmol, 29.3 % yield) as a white solid. LC-MS Anal.Calc’d for CuH8F2N20 222.06, found [M+H] 223.0.

The chemical industry reduces the impact on the environment during synthesis 62802-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HERNANDEZ, Andres S.; ELLSWORTH, Bruce A.; EWING, William R.; CHEN, Bin; WO2014/78608; (2014); A1;,
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Related Products of 186046-78-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 186046-78-6, name is 2-(4-(((Benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid, molecular formula is C20H17N3O5, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 60 1-(5-Chloro-benzothiazole-2-sulfonyl)-4-{[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-piperazin-2-one The title compound was synthesised by the reaction of 1-(5-chloro-benzothiazole-2-sulfonyl)-piperazin-2-one trifluoroacetic acid salt with [4-N-(benzhydryloxycarboniyl)-cytosin-1-yl]-acetic acid as per the procedure of Example 52. 1H NMR (500 MHz; DMSO-d6) delta 10.98 (brs, 1H), 8.40 (m, 2H), 7.96 (s, 1H), 7.79 (m, 1H), 7.45 (d, 4H), 7.38 (t, 4H), 7.30 (t, 2H), 6.96 (t, 1H), 6.80 (s, 1H), 4.83 (s, 2H), 4.72 (s, 0.8H), 4.46 (s, 0.8H), 4.28 (s, 1.2H), 4.22 (t, 1.2H), 4.06 (t, 0.8H), 3.99 (t, 1.2H), 3.87 (t, 0.8H).

According to the analysis of related databases, 186046-78-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kim, Sung Kee; Lee, Hyunil; Lim, Jong Chan; Choi, Hoon; Jeon, Jae Hoon; Ahn, Sang Youl; Lee, Sung Hee; Yoon, Won Jun; US2003/225252; (2003); A1;,
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Synthetic Route of 932-52-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a mixture of 5-aminouracil (127 mg, 1 mmol) with an appropriate aldehyde (241 mg, 1.2 mmol) in methanol (15 mL) were added few drops of glacial acetic acid. The reaction mixture was stirred at room temperature until 5-aminouracil was completely consumed (TLC). The precipitate was filtered off, washed with methanol and air dried to give the corresponding product 1-10 as a yellow solid.

According to the analysis of related databases, 932-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koz; Russian Journal of General Chemistry; vol. 89; 1; (2019); p. 122 – 127; Zh. Obshch. Khim.; vol. 89; 1; (2019); p. 122 – 127,6;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate

(R)-tetrahydro-2H-pyran-3-amine hydrochloride (1.00 g, 7.27 mmol) in acetonitrile (5 ml) was added dropwise to a mixture of DIPEA (3.16 ml, 18.2 mmol) and ethyl 2,4- dichloropyrimidine-5-carboxylate (1.61 g, 7.27 mmol) in acetonitrile (30 ml) at 0C over a period of 5 minutes under air. The resulting suspension was stirred for 4 h, slowly allowing to warm to rt and stirred at rt overnight. The reaction mixture was evaporated to dryness to remove MeCN, diluted with EtOAc (100 mL), and washed with water then sat. brine. The organic layer was dried over MgS04, filtered and evaporated. The resulting crude product was purified by fee, elution gradient 0 to 50% EtOAc in heptane, to afford the title compound (0.936 g, 45%) as a yellow oil; 1H NMR (400 MHz, DMSO) 1.33 (3H, t), 1.57 (1H, dt), 1.71 (2H, dtd), 1.91 (1H, ddt), 3.48 (1H, dd), 3.55 – 3.66 (2H, m), 3.75 (1H, dd), 4.11 – 4.2 (1H, m), 4.33 (2H, q), 8.58 (1H, d), 8.65 (1H, s); m/z MH+286.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; TING, Attilla, Kuan, Tsuei; (103 pag.)WO2018/114999; (2018); A1;,
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Application of 2927-71-1 ,Some common heterocyclic compound, 2927-71-1, molecular formula is C4HCl2FN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a stirred solution of (S)-tert-butyl 3-aminopiperidine-1-carboxylate (1) (1.437 g, 7.18 mmol) in DMF (10 mL) was added DIPEA (1.56 mL, 8.98 mmol) and 2,4-dichloro-5- fluoropyrimidine (2) (1.0 g, 5.98 mmol) in DMF (2 mL) at 0 C drop wise. The reaction mixture was allowed to stir at room temperature for 16 h. After consumption of starting material by TLC (absence of compd-2), the mixture was diluted with ether (75 mL) and washed with ice cold water (3 x 50 mL), brine solution (25 mL), dried over sodium sulfate and concentrated under reduced pressure to afford tert-butyl (S)-3-((2-chloro-5- fluoropyrimidin-4-yl)amino)piperidine-1-carboxylate (3) (1.670 g, 5.06 mmol, 84 % yield) as white solid. TLC system: 30% EA in pet Ether Rf: 0.5 LCMS (ESI): m/z 331.44 (M+1)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2927-71-1, its application will become more common.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina, C.; LEE, Sam SK; FEESE, Michael, David; (206 pag.)WO2020/23813; (2020); A1;,
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Electric Literature of 10244-24-3, Adding some certain compound to certain chemical reactions, such as: 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine,molecular formula is C12H17ClN4O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 10244-24-3.

A solution of 40 g of 2,4-[bis-morpholino]-6-chloropyrimidine and 34 g of piperazine in 60 g of pyridine is heated at 100 for 24 h. The mixture is partitioned between methylene chloride and aqueous potassium carbonate. The organic phase is filtered through sodium sulfate and concentrated. The residue is chromatographed (methylene chloride to 4% methanol/1% ammonium hydroxide/methylene chloride) to give the title compound, NMR (CDCl3) 2.90, 3.50, 3.75, 3.80 and 5.10 delta.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 10244-24-3, 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Upjohn; US5120843; (1992); A;,
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Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7355-55-7, name is 2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one

The G005 (10. 0g, 66. 6mmol) was added to lOOmLPOCl3, refluxed for 2h, the solvent spin After cooling to room temperature, the reaction was added to 120mL of ice water, and the solid was filtered, and the filtrate was washed with aqueous ammonia solution to pH = 2, and the ice bath and the precipitate As 2h after filtration, the solid was filtered and washed first with ice water 10mL, 30mL second ice was washed with ether, was drained after 8. 7g, 78% yield .

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 7355-55-7, 2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one.

Reference:
Patent; SHANGHAIJIAO TONG UNIVERSITY; EASTCHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY; SHEN, YUMEI; TANG, DAONIAN; SHAO, ZHIFENG; GONG, BING; LIU, YAZHI; WU, XINYAN; ZHAO, XIAODONG; LI, XIAOWEI; WEI, XIAOFEI; HU, YU; (21 pag.)CN103819523; (2016); B;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 31462-54-1, name is 2-Iodopyrimidine. A new synthetic method of this compound is introduced below., name: 2-Iodopyrimidine

Add in the reaction tube2-iodopyrimidine (0.5 mmol, 1.0 eq.)And sodium dithionite (0.55mmol, 1.1 equivalent),Replace the air in the test tube with high purity nitrogen.Add 3 mL of N,N-dimethylformamide as solvent.The reaction was stirred for 16 hours (purity of 98%) by heating to 90 C.After the reaction was cooled, tetrabutylammonium iodide (0.05 mmol, 0.1 equivalent) and potassium iodide (0.6 mmol, 1.2 equivalent) were added to the reaction mixture.And 4-methylbenzyl bromide (1.0 mmol, 2.0 eq.),Replace the air in the test tube with high purity nitrogen.Stir at room temperature for 10 hours.The reaction was quenched with saturated brine.Extracted with ethyl acetate,Combine the organic phase,dry,Concentrate and separate by column chromatography.The target product Ib was obtained in 76% yield.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 31462-54-1, 2-Iodopyrimidine.

Reference:
Patent; Jiaxing College; Qiu Guanyinsheng; Li Yuewen; Wu Jie; (13 pag.)CN109180572; (2019); A;,
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