Pyrimidines

Reference of 1546-78-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1546-78-7 as follows.

Take 0.17g (0.001mol) 4- hydroxy-6-trifluoromethyl-pyrimidine (prepared as described in Example 1), 0.23g (0.001mol) 4- chloro-1- (4-chlorophenyl) -1H – pyrazole (prepared as in Example 2), 0.14g (0.001mol) of potassium carbonate in 50ml single neck flask, 10mlN, N- dimethylformamide as a solvent, was heated to 100 deg.] C, the reaction 4-10 hours, TLC after completion of the reaction was monitored, the solvent was distilled off under reduced pressure, was added (3 × 50ml) and extracted with ethyl acetate, the organic phase was washed with saturated brine 50ml, after solvent removal the residue by column chromatography (eluent, ethyl acetate and petroleum ether , a volume ratio of 1: 2) to obtain 0.26 g of a white solid, yield 72.5%,

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1546-78-7, its application will become more common.

Reference:
Patent; Shenyang Sinochem Agrochemicals R&D Co., Ltd.; Sun, Xufeng; Guan, Aiying; Zhao, Jie; Ma, Sen; Sun, Qin; Chen, Xuanming; Liu, Zhangling; (40 pag.)CN105777717; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1683-75-6, 2-Amino-4-chloro-5-fluoropyrimidine, 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, HPLC of Formula: C4H3ClFN3, blongs to pyrimidines compound. HPLC of Formula: C4H3ClFN3

General procedure: To a mixture of (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1H-benzo[d]imidazole derivatives (7 mmol, 1 eq.), which was commercially available or prepared according to the literature procedure [WO2016192630], amino aromatic chloride (1.1 eq.) in DMF (20 mL) was added Na2CO3 aq. (3 eq.). The mixture was bubbled with Ar for 15 mins and then Pd(dppf)Cl2 (0.1 eq.) was added. The mixture was heated to 80oC and stirred for 4-6 hours under Ar atmosphere, then cooled to room temperature and concentrated to remove the organic solvent after reaction completion. The residue was diluted with water (100 mL) and extracted with EA (150 mL×3). The organic layer was separated and washed with saturated brine, then dried with anhydrous Na2SO4. The organic phase was then concentrated and the residue was further purified with flash chromatography or preparative HPLC to afford the desired intermediate compounds 3a-3j, which were characterized by LC-MS.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1683-75-6, 2-Amino-4-chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Zha, Chuantao; Deng, Wenjia; Fu, Yan; Tang, Shuai; Lan, Xiaojing; Ye, Yan; Su, Yi; Jiang, Lei; Chen, Yi; Huang, Ying; Ding, Jian; Geng, Meiyu; Huang, Min; Wan, Huixin; European Journal of Medicinal Chemistry; vol. 148; (2018); p. 140 – 153;,
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Reference of 50270-27-4, 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.50270-27-4, name is 2,4,6-Trichloropyrimidine-5-carbaldehyde, molecular formula is C5HCl3N2O, molecular weight is 211.4332, as common compound, the synthetic route is as follows.

N-{4-[1-(1-benzylpiperidin-4-yl)-4-(3,6-dihydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}acetamide (Scheme 6)Example 3To a solution of 2,4,6-trichloro-pyrimidine-5-carbaldehyde (1.53 g, 7.19 mmol) in anhydrous ethanol (25 mL) at -78° C. was added (1-benzyl-piperidin-4-yl)-hydrazine hydrochloride (2 g, 7.19 mmol) and triethylamine (5.01 mL). After 30 min allow the reaction mixture to warm to 0° C. After 1 h warm to 25° C. Add ethyl acetate and extract with saturated aqueous sodium bicarbonate, water (2.x.) and brine. Dry over anhydrous magnesium sulfate. Concentrate in vacuo to give an oil. Add diethyl ether and remove precipitate by filtration. Concentrate mother liquor and add diethyl ether and remove precipitate by filtration. Add 2N HCl in diethyl ether to mother liquor and collect the precipitate. 1-(1-Benzyl-piperidin-4-yl)-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine hydrochloride is obtained as a white solid is obtained. A mixture of this white solid (530 mg, 1.34 mmol), tributyl-(3,6-dihydro-2H-pyran-4-yl)-stannane (500 mg), PdCl2(PPh3)2 (50 mg), diisopropylethyl amine (230 muL) in dimethylformamide (6 mL) is heated to 70° C. After 3 h at 70° C. and 18 h at 60° C.° the dimethylformamide is removed in vacuo. The residue is dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic phase is dried over anhydrous magnesium sulfate and concentrated in vacuo to give a dark oil. The oil is treated with 4-acetamidophenylboronic acid (72 mg, 0.402 mmol), Pd(PPh3)4 (5 mg) and 2M aqueous sodium carbonate (0.281 mL, 0.563 mmol) in dimethoxyethane (1 mL) and heated in a microwave at 175° C. for 15 min. The reaction mixture is purified by reverse phase HPLC (CH3CN/H2O/CF3CO2H) followed by silica gel chromatography (CH2Cl2/MeOH) to give the title compound as a trifluoroacetate salt (7.7 mg).

The chemical industry reduces the impact on the environment during synthesis 50270-27-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wyeth; US2009/192176; (2009); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 2434-56-2, Adding some certain compound to certain chemical reactions, such as: 2434-56-2, name is 4,6-Diaminopyrimidine,molecular formula is C4H6N4, 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 2434-56-2.

Compound 2~(5-chloro-2,4-dimethoxypheny])imidazo[l ,2-c]pyrimidin-7-amme 195 was prepared in the same manner as 2-(5-chloro-2,4-dimethox phenyl)-7-(pyrrolidin-l – yl)-imidazo[l ,2-o]pyridine 5a. Solid was basified with aqueous ammonia, washed with water, collected by filtration and dried. The product was obtained as a white solid (52 mg, 18% yield). 1H NMR (300 MHz, DMSO-d6): delta 8.96 (s, III), 8.14 (s, 1H), 7,99 (s, 1 H), 6.87 (s, 1H), 6.15 (tn, 2H), 4.01 (s, 3H), 3.94 (s, 3H); HPLC (Method 3) 95.12% (AUC), = 16.24 niin; ESI MS m/z 305 [M+H|+. A solution of 2-bromo-1-(5-chloro-2,4-dimethoxyphenyl)ethanone 3 (70 mg, 0.24 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 4a (39 mg, 0.24 mmol) in acetone (3 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration, washed with acetone, and dried under reduced pressure to afford 2-(5-chloro-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1 ,2-a]pyridine hydrobromide 5a (45 mg, 43%) as a pink solid. 1H NMR (300 MHz, DMSO-d6) . delta 13.03 (s, 1H), 8.50 (d, J = 7.6 Hz, 1H). 8.20 (s, 1H), 7.89 (s, 1H), 6.97 (s, 1H), 6.95 (dd, J=2.2, 7.6 Hz, 1H), 6.30 (d, J= 2.0 Hz, 1H), 4.05 (s, 3H), 3.99 (s, 3H). 3.48-3.38 (m, 4H), 2.08- 1.98 (m, 4H); HPLC ( Method 4) 98.7% (AUG), tR = 19.02 min. APCI MS m/z 358 [M + H]+ .

According to the analysis of related databases, 2434-56-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 42754-96-1 , The common heterocyclic compound, 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, 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.

Add 4,6-dichloro-1H-pyrazolo [3,4-d] pyrimidine 1a (120 mg, 0.63 mmol),4-methoxybenzylamine 1b (87.1 mg, 0.63 mmol)And triethylamine (64.13 mg, 0.63 mmol) were dissolved in 2 mL of a tetrahydrofuran solution and stirred at room temperature for 1 hour.The reaction was stopped and distilled under reduced pressure. The residue was purified by silica gel column chromatography using eluent system A,The title product 1c (140 mg) was obtained in a yield of 76.1%.

The synthetic route of 42754-96-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Yang Shibo; You Lingfeng; Feng Jun; He Feng; (49 pag.)CN110526918; (2019); A;,
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Related Products of 69034-12-4, 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.69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

To a stirred solution of methyl-2-(2-fluorophenyl)-2-(4-(4,4,5,5-tetramethyl- l ,3,2-dioxaborolan-2-yl)phenyl)acetate (1.83 g, 4.8 mmol) in dioxane (80 mL) and water (20 mL) was added 2-chloro-5-trifluoromethylpyrimidine (1.0 g, 5.5 mmol) and K2C03 (1.35 g, 9.8 mmol). The mixture was degassed with N2 for 5 min, treated with Pd(PPh3)4 (280 mg, 0.24 mmol) and heated at 110 C overnight (LCMS indicated completion of the reaction). The mixture was cooled to r.t., treated with water (100 mL) and extracted with DCM (2 x 100 mL). The combined organic phase was separated, dried (MgS0 ), and evaporated in vacuo. Purification by chromatography (Si02) eluting with isohexane/ethyl acetate (95:5) afforded the subtitle compound as a white solid (1.45 g, 74% yield). LCMS (Rt 3.54 min, [M+H]+ 391). N.M.R. (CDC13) 9.01 (s, 2H), 8.48 (d, 2H, J = 8.4 Hz), 7.47 (d, 2H, J = 8.4 Hz), 7.30-7.25 (m, 2H), 7.13-7.05 (m, 2H), 5.38 (s, 1H), 3.78 (s, 3H).

Statistics shows that 69034-12-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-(trifluoromethyl)pyrimidine.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; MUNOZ-SANJUAN, Ignacio; BEAUMONT, Vahri; BECONI, Maria; BUeRLI, Roland, W.; HAUGHAN, Alan, F.; LUCKHURST, Christopher, A.; WALL, Michael; RAPHY, Gilles; THOMAS, Beth; WO2014/159210; (2014); A1;,
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Pyrimidine – Wikipedia

Reference of 89581-38-4 ,Some common heterocyclic compound, 89581-38-4, molecular formula is C6H5BrN2O2, 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 mixture of methyl 5-bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol) and copper (I) cyanide (1.92 g, 21.4 mmol) in a 100 mL round bottom flask was added DMA (21 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 5 min. The reaction mixture was heated to 110 C for 2 d and cooled to room temperature. The reaction mixture was diluted with EtOAc and water and filtered through a glass frit (medium). The filtrate was transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4 x) and the combined organic extracts were washed with brine (1 x), dried over MgSO4, filtered, concentrated to give a yellow oil. Purification by flash column chromatography on silica gel (80 g, 5% to 50% EtOAc in heptane) gave methyl 5-cyanopyrimidine-2-carboxylate (0.83 g, 5.08 mmol, 48% yield) as a white solid. LC/MS (ESI+) m/z = 164.0 (M+H).

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. 89581-38-4, Methyl 5-bromopyrimidine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); A1;,
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Pyrimidine – Wikipedia

Application of 1445-39-2, 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 1445-39-2, name is 2-Amino-5-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

2-Amino-5-iodopyrimidine (2.21 g), bis (triphenylphosphine) palladium dichloride (350 mg) and copper (I) iodide (40 mg) were stirred in DMF (100 mL)- triethylamine (20 mL) and degassed with nitrogen for 10 min. 3-Ethynyl aniline (1.29 g) was added and the mixture heated to 95 C for 2 hours. The solvent was evaporated and the residue was purified by trituration with DCM (20 mL) to give the title compound as a brown solid (1.25 g, 60%); ‘H NMR (DMSO-d6) 5.21 (bs, 2H), 6.58-6. 70 (m, 3H), 7.03-7. 07 (m, 3H), 8.40 (s, 2H); MS m/e MH+ 211.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1445-39-2, 2-Amino-5-iodopyrimidine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/60970; (2005); A1;,
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Pyrimidine – Wikipedia

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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., name: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

(A) 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5 g, 32.6 mmol) in THF (50 mL) was added NaH (30%, 4 g, 50.0 mmol) at 0 C. The reaction mixture was stirred at 0 C. for 1 hour before the addition of (2-(chloromethoxy)ethyl)-trimethylsilane (15 g, 90.0 mmol). The reaction was stirred at ambient temperature for 3 hours. It was then treated with water (5 mL) and extracted with EtOAc. The organic layer was concentrated under reduced pressure, and the residue was purified by chromatography to give the title compound. MS (m/z): 284 (M+H)+ (35Cl), 286 (M+H)+ (37Cl).

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, 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Su, Wei-Guo; Deng, Wei; Li, Jinshui; Ji, Jianguo; US2013/210831; (2013); A1;,
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Pyrimidine – Wikipedia

Application of 1722-12-9, 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 1722-12-9, name is 2-Chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 2-chloropyrimidines(10 mmol), potassium cyanide (13-15 mmol), water (20 mmol), and DMSO(20 mL) was heated to 60 C. A solution of 3-quinuclidinol (0.1-0.2 mmol) inDMSO(5 mL) was added to the reaction mixture over 0.5 h. The reaction mixturewas stirred at 50-70 C for additional hours as specified in Table 1. Uponcompletion, the mixture was cooled to room temperature and water (50 mL) wasadded. The resulting mixture was extracted with isopropyl acetate (3 40 mL)(product 7a precipitated out after water addition and was collected by filtration).The combined organic layers were washed with water (2 30 mL), dried overMgSO4, filtered, and concentrated under vacuum to give crude 2-cyanopyrimidines, which were purified by column chromatography (SiO2) to afford pureproducts.

According to the analysis of related databases, 1722-12-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Hong-Yong; Shieh, Wen-Chung; Prashad, Mahavir; Tetrahedron Letters; vol. 55; 36; (2014); p. 5055 – 5057;,
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Pyrimidine – Wikipedia