Day: June 3, 2021

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. 109-12-6, name is Pyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C4H5N3

A 5 L three-necked round bottom flask was charged with 2-aminopyrimidine (285.30 g, 3 mol), N-bromosuccinimide (1.17 kg, 6.6 mol), acetonitrile 2 L and methanol 1 L. The mixture in the reaction flask was stirred at 70 C for 6 hours. TLC and HPLC confirmed the reaction was complete. After the reaction was completed, the solvent was removed by rotary evaporation to give the crude product. The crude product was concentrated by evaporation and recrystallized to give the pure product 2-amino-5-bromopyrimidine. After drying, the yield was 90.48% and the purity was 99.05% (HPLC).

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, 109-12-6, Pyrimidin-2-amine.

Reference:
Patent; Shandong Youbang Biochemical Technology Co., Ltd.; Geng Xuanping; Zhang Xianglong; Cheng Wei; Lai Xinsheng; Lai Chao; Lai Ziteng; (4 pag.)CN106632079; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-66-9, 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 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

To a 5 mL vial containing a stir bar, 3-(2-aminopyrimidin-5-yl)-6-cyclobutyl-2-fluorophenol (80 mg, 0.31 mmol) and 2-chloropyrimidine (41 mg, 0.34 mmol) were added Cs2CO3 (203 mg, 0.62 mmol) and DMSO (0.8 mL). The resultant mixture was stirred at 120 Celsius for approximately 1 hour via microwave irradiation. The reaction mixture was cooled to room temperature before passing the mixture through a syringe filter and subjecting the filtrate to FCC to afford the title compound (81 mg, 78%). The title compound was prepared using conditions similar to those described in Example 160 heating at 80 Celsius via microwave radiation for 2 hours and using 2-chloropyrimidine-4-carboxamide. MS (ESI): mass calcd. for C19H17FN6O2, 380.14; m/z found, 381.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 8.81 (d, J=4.9, 1H), 8.44 (s, 2H), 8.21 (s, 1H), 7.98 (s, 1H), 7.77 (d, J=4.9, 1H), 7.52-7.42 (m, 1H), 7.30 (d, J=8.2, 1H), 6.89 (s, 2H), 3.63-3.51 (m, 1H), 2.15-2.00 (m, 4H), 1.99-1.84 (m, 1H), 1.81-1.68 (m, 1H).

According to the analysis of related databases, 22536-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 38275-55-7, 5-Fluoropyrimidine-2-carbonitrile, 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, Computed Properties of C5H2FN3, blongs to pyrimidines compound. Computed Properties of C5H2FN3

Method 12; N-(l-(5-Fluoropyrimidin-2-yl)vinyl)acetamide; 5-Fluoropyrimidine-2-carbonitrile (Method 6, 1.0 g, 8.1 mmol) in THF (10 ml) was added a solution of MeMgBr (3.3 ml, 9.75 mmol) in ether drop wise at 0 0C. After addition, the reaction was warmed to room temperature, stirred at room temperature for 1 hour and then diluted with DCM (10 ml). Acetic anhydride (1.23 ml, 13.0 mmol) was added in one portion. The reaction was stirred at room temperature for 1 hour and 40 0C for 1 hour. Saturated sodium bicarbonate solution (10 ml) was added and extracted with EtOAc (2×20 ml). The combined organic was dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography (hexane-EtOAc = 2.5 : 1) to give the title compound as a white solid (0.38 g, 26%). 1H nuMR (400 MHz) 9.34 (s, IH), 8.95 (s, 2H), 6.25 (s, IH), 6.03 (s, IH), 2.11 (s, 3H). MS: Calcd.: 181; Found: [M+H]+ 182.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38275-55-7, 5-Fluoropyrimidine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/49041; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 32779-36-5, 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 32779-36-5, name is 5-Bromo-2-chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromo-2-chloropyrimidine (2 g, 10.34 mmol) and dimethylamine (5 ml, 10.00 mmol) in tetrahydrofuran (2 ml_) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography 5%EtOAc/PE) to give 5-bromo-N,N-dimethylpyrimidin-2-amine (1 .9 g, 8.93 mmol, 86 % yield) as a white solid. LCMS: [M+H] 202.

According to the analysis of related databases, 32779-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JIN, Qi; POHLHAUS, Denise Teotico; SPLETSTOSER, Jared; (320 pag.)WO2017/98440; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1005-37-4 ,Some common heterocyclic compound, 1005-37-4, molecular formula is C5H7ClN4, 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.

General procedure: General Procedure 5: To a mixture of a suitable chloropyrimidine derivative (1 equiv.) in DMF/water (9:1) is added the appropriate boronic acid (or boronic ester) derivative (1.1 equiv.), Na2003 (2 equiv.) and Pd(PPh3)4 (0.1 equiv.). The mixture is heated at 120 00 overnight or in the microwave until the reaction iscomplete as shown by LCMS. The crude mixture is then purified by preparative HPLC to afford the desired product.Example 696-(4-tert-butylphenyl)-4-N-methylpyri midi ne-2,4-diam me.Prepared according to general procedure 5 from (4-tert-butylphenyl)boronic acidand 6-chloro-4-N-methylpyrimidine-2,4-diamine. LCMS [M+H] 257; 1H NMR (400MHz, CD3OD) OH 7.77 (2H, d, J = 8.7 Hz), 7.53-7.48 (2H, m), 6.22 (1H, s), 2.93 (3H, s), 1.38 (9H, s).

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. 1005-37-4, 6-Chloro-N4-methylpyrimidine-2,4-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; HELLEDAY, Thomas; KOOLMEISTER, Tobias; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; WO2014/84778; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, 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. SDS of cas: 374930-88-8

To a solution of dicyclohexylamine (3.43 g, 18.94 mmol) in THF (60 mL) at -78 C. was added n-BuLi (2.5 M, 7.9 mL, 18.94 mmol) dropwise. The mixture was stirred at RT for 10 min, followed by the addition of methyl 2-(4-fluorophenyl)acetate (2.69 g, 16.02 mmol) in toluene (60 mL). After stirred at RT for another 10 min, tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (5.0 g, 14.57 mmol), Pd2(dba)3 (667 mg, 0.728 mmol) and P(t-Bu)3 (10%, 1.47 g, 0.728 mmol) were added sequentially. The reaction mixture was stirred at RT for 15 h, quenched by water (150 mL) and extracted with EA. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was passed a column (silica gel, PE_EA=6:1) to afford the title compound (0.5 g, 8%) as an orange solid. MS (ES+) C22H27FN4O4 requires: 430. found: 431 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 374930-88-8.

Reference:
Patent; Hodous, Brian L.; Kim, Joseph L.; Wilson, Kevin J.; Wilson, Douglas; Zhang, Yulian; US2015/111887; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4595-60-2, 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 4595-60-2 as follows.

A mixture of 4-chloro-3-nitrophenylboronic acid (520 mg, 2.58 mmoles), 2-bromopyrimidine (410 mg, 2.58 mmoles), tetrakis(triphenylphosphine)palladium(0) (100 mg, 0.08 mmoles) and sodium carbonate (800 mg, 7.5 mmoles) in water (2.5 ml_) and dimethylformamide (15 ml_) was heated at 1000C for 1hour. Water was added and the mixture extracted with ethyl acetate (x2). The combined extracts were dried and evaporated then chromatographed (dichloromethane-methanol) to give the title compound (390 mg, 64%). 1 H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.32 (t, J=4.93 Hz, 1 H) 7.69 (d, J=8.59 Hz, 1 H) 8.64 (dd, J=8.34, 2.02 Hz,1 H) 8.87 (d, J=5.05 Hz, 2 H) 9.02 (d, J=2.02 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-60-2, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/127458; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 330786-24-8, Adding some certain compound to certain chemical reactions, such as: 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine,molecular formula is C17H13N5O, 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 330786-24-8.

9g tri-n-butylphosphine dissolved in 100mL anhydrous tetrahydrofuran and cooled down to 0-5 degrees.9g of diisopropyl azodicarboxylate was added dropwise under N2 protection. After the addition was completed,The reaction temperature was controlled at 0-5 degrees for 1 h. The above tributylphosphine andA mixture of diisopropyl azodicarboxylate was slowly poured into 4 g of solution3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine andIn 3.5 g of (S)-1-Boc-3-hydroxypiperidine in 50 mL of anhydrous tetrahydrofuran,Stir 0-5 degrees overnight. After the reaction liquid is concentrated under reduced pressure,Purification by column to obtain the product 6.8g, yield 75%

According to the analysis of related databases, 330786-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Fupu Biological Technology Co., Ltd.; Liu Zheng; (13 pag.)CN106279284; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5177-27-5, 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.5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, molecular weight is 163.9927, as common compound, the synthetic route is as follows.

A mixture of Pd(OAc)2 (20 mg, 0.070 mmol), PPh3 (80 mg, 0.30 mmol), potassium (2-furyl)trifluoroborate (530 mg, 3.00 mmol), K2CO3 (340 mg, 2.46 mmol), and 2,4-dichloropyrimidine-5-amine (8d) (200 mg, 1.20 mmol) in EtOH (50 mL, 96%) was stirred at 80 C for 16 h under Ar, and evaporated in vacuo. The product was purified by flash chromatography on silica gel eluting with EtOAc/CH2Cl2/hexane (1:5:5); yield 220 mg (80%), mp 173-175 C (dec), yellow solid. 1H NMR (CDCl3, 300 MHz) delta 8.28 (s, 1H, H-4), 7.62 (dd, J=1.7, 0.8 Hz, 1H, H-5 in furyl), 7.53 (dd, J=1.7, 0.8 Hz, 1H, H-5 in furyl), 7.37 (dd, J=3.5, 0.8 Hz, 1H, H-3 in furyl), 7.12 (dd, J=3.5, 0.8 Hz, 1H, H-3 in furyl), 6.61 (dd, J=3.5, 1.7 Hz, 1H, H-4 in furyl), 6.50 (dd, J=3.5, 1.7 Hz, 1H, H-4 in furyl), 3.86 (br s, 2H, NH2); 13C NMR (CDCl3, 75 MHz) delta 153.3 (C-2 in furyl), 152.5 (C-2 in furyl), 148.7 (C-2, C-5, or C-6), 145.8 (C-4), 144.0 (C-5 in furyl), 143.8 (C-5 in furyl), 139.1 (C-2, C-5, or C-6), 134.1 (C-2, C-5, or C-6), 112.8 (C-3 in furyl), 112.4 (C-4 in furyl), 112.0 (C-4 in furyl), 110.4 (C-3 in furyl); MS EI m/z (rel %) 227 (100, M+), 198 (37), 171 (7), 114 (6), 78 (6); HRMS (EI) calcd for C12H9N3O2: 227.0695. Found 227.0694.

The chemical industry reduces the impact on the environment during synthesis 5177-27-5, I believe this compound will play a more active role in future production and life.

Reference:
Article; Read, Matthew L.; Krapp, Andreas; Miranda, Pedro O.; Gundersen, Lise-Lotte; Tetrahedron; vol. 68; 7; (2012); p. 1869 – 1885;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3177-24-0, 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 3177-24-0 as follows.

[00607] General conditions for the preparation of 2-amino-4-chloropyrimidine-5-carbonitrile:[00608] To a solution of 2,4-dichloropyrimidine-5-carbonitrile (E-1) (2.0 g, 11.5 mmol) in 1,4-dioxane (20 mL) at 0 C, ammonium hydroxide (28-30%, 4.4 mL, 34.5 mmol) is added dropwise, and the resulting mixture is stirred while warming from 0 C to RT for 2 h. Then, the mixture is partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer is washed with brine, dried over Na2SO4 and filtered. The filtrate is mixed with silica gel and then concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0- 100% ethyl acetate/hexanes to afford the product (E-2) (917 mg) and a mixture of (E-2) and (E-3). Additional (E-3) can be obtained from this mixture by a second column chromatographic purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2015/168079; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia