Tag: M.W=300-400

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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, 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. Safety of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

A mixture of 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (32a) (0.20 g, 0.51 mmol) and 1-(ethoxycarbonylmethyl)piperazine (33) (0.17 g, 1.01 mmol) in 4 mL of EtOH was heated with a CEM Discover microwave at 250 W, Pmax 150 C. for 45 min. The resulting mixture was treated with EtOH (6 mL) and then stirred at rt for 1 h. The solid was collected on a filter to give 0.24 g of ethyl 2-(4-(6-(5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-ylamino)-2-methylpyrimidin-4-yl)piperazin-1-yl)acetate (34a) (89% yield). HPLC>99% pure (Rt 2.517 min); LC/MS (ES-) 530/532 (M+H, 100); 1H NMR (DMSO-d6) delta 11.48 (s, 1H), 9.86 (s, 1H), 8.22 (s, 1H), 7.40 (m, 1H), 7.28 (m, 2H), 6.06 (s, 1H), 4.10 (q, J=7.1 Hz, 2H), 3.53 (s, 4H), 3.29 (s, 2H), 2.59 (t, J=4.6 Hz, 4H), 2.41 (s, 3H), 2.24 (s, 3H), 1.20 (t, J=3H); Anal. Calcd for C24H28ClN7O3S: C, 54.38; H, 5.32; Cl, 6.69; N, 18.50; S, 6.05. Found:: C, 54.24; H, 5.16; Cl, 6.80; N, 18.59; S, 6.09.HPLC conditions column: YMC ODS-A S5 4.6×50 mm; UV: 220 nm; gradient time: 4 min; flow rate: 4 mL/min, 0-100% B; solvent A: 10% MeOH/90% H2O with 0.2% H3PO4, solvent B: 90% MeOH/10% H2O with 0.2% H3PO4.

With the rapid development of chemical substances, we look forward to future research findings about 302964-08-5.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/219370; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

EXAMPLE 1; Preparation of the Compound of Formula (II); In a 50 mL round bottomed flask equipped with a magnetic stirrer, condenser, Ar inlet, temperature controller (J-Kem) and heating mantle was introduced compound (1) (1.0 g, 2.53 mmoles, HPLC 95.28%), N-methylpyrrolidone (6.5 mL), piperazine (0.26 g, 3.043 mmoles, 1.2 eqs) and diisopropylethylamine (0.88 mL, 5.072 mmoles, 2 eqs). The suspension was heated at 120 C. for 45 min (HPLC showed 56.3% (II), 21.1% (2) and 0.6% of starting (1)). The mixture was cooled at r.t. and diluted slowly with water (27.8 mL) to precipitate the product. The solid was collected by filtration and rinsed with water (14 mL). The solid collected showed only 45.2% of (II) along with 31.4% (2)). A white solid also crystallized out of the filtrate. The material was collected by filtration and dried under high vacuum at 40 C. for 16 hrs to give 0.22 g (0.49 mmole, 19.6% yield) of (II) as a white solid (HPLC 86.9%). HPLC system. Column; Luna C-18, 4.6×75 mm, 3 u Mobile phase A; 100% H2O+0.05% TFA Mobile phase B; 100% CH3CN+0.05% TFA Gradient; 1% B to 95% B in 15 min, hold 95% B for 2 min Flow Rate; 1 mL/min Inj. Volume; 5 uL Detection; 255 nm Column temperature; 25 C. Retention times; (II) (7.04 min), (2) (9.70 min), (1) (10.73 min). 1H NMR (400 MHz, DMSO-d6) delta 9.85 (s, 1H), 8.20 (s, 1H), 7.39 (d, 1H, Ph, J=7.6 Hz), 7.28 (d, 1H, Ph, J=7.1 Hz), 7.24 (t, 1H, Ph, J=7.7 Hz), 6.01 (s, 1H), 3.43 (m, 4H, piperazine), 2.73 (m, 4H, piperazine), 2.39 (s, 3H, CH3), 2.23 (s, 3H, CH3) ES+ MS m/z (rel. intensity) 444 (MH+, 100)

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, 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; Arora, Vinod Kumar; Christopher, Lisa Joy; Cui, Donghui; Li, Wenying; US2006/211705; (2006); 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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine, molecular formula is C16H30N2Sn, 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. Formula: C16H30N2Sn

A mixture containing 4tau(4-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.29 mmol), 2-tributylstannanyl-pyrimidine (130 mg, 0.36 mmol), cesium fluoride (85 mg, 0.56 mmol) and palladium di-tert-butylphosphine was degassed three times with Ar. Dioxane was added and the formed reaction mixture was stirred at 90 0C overnight under Ar. Then the reaction mixture was filter through celite and the solvent was removed under vacuum and crude product was used directly in the next step.

With the rapid development of chemical substances, we look forward to future research findings about 153435-63-3.

Reference:
Patent; SCHERING CORPORATION; WO2007/97937; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 330794-31-5, 1-Cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, 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, 330794-31-5, blongs to pyrimidines compound. Quality Control of 1-Cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Synthesis of 1-(3-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)ethanone (BA81, BA81d & BA81dd); A solution of tert-butyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (200 mg, 0.76 mmol) in EtOH (3.3 ml) was added to a solution of 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA80, 100 mg, 0.30 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified using silica gel column chromatography [MeOH-CH2Cl2, 5:95] yielding BA81. BA81 was dissolved in 50:50 CH2Cl2:TFA and stirred for one hour at room temperature. The reaction mixture was concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81d. BA81d was dissolved in CH2Cl2 (2 ml) and BBr3 (4 mL, 4 mol) was added slowly with a syringe, while stirring. The reaction was stirred at room temperature for 2 hours then concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81dd.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,330794-31-5, its application will become more common.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1197953-49-3, 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 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. This compound has unique chemical properties. The synthetic route is as follows.

171 mg of compound c25-12 and 165 mg of compound b3-1 were dissolved in 13 mL of ethylene glycol monomethyl ether and 0.43 mL of ethanol, and 0.26 mL of a hydrogen chloride solution (5.6 M) was added thereto, and the mixture was reacted at 120 C for 18 hours.The solvent was removed under reduced pressure, water was added to PH 9 with potassium carbonate, extracted with dichloromethane, dried, concentrated, obtained by column chromatography 24mg compound c-25;

According to the analysis of related databases, 1197953-49-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Tongyuankang Pharmaceutical Co., Ltd.; Wu Yusheng; Zhi Wubin; Wang Xin; Wu Shiyong; Li Jingya; Guo Ruiyun; Zheng Maolin; Liang Apeng; Wang Guohui; Chen Mingtao; Ma Jie; Niu Chengshan; (65 pag.)CN108689994; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)pyrimidine, 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, Safety of 2-(Tributylstannyl)pyrimidine, blongs to pyrimidines compound. Safety of 2-(Tributylstannyl)pyrimidine

EXAMPLE 889-Amino-2-cyclobutyl-5-pyrimidin-2-yl-2,3-dihydropyrrolo[3,4-b]quinolin-1-one9-amino-5-bromo-2-cyclobutyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one (306 mg, 0.92 mmol), CombiPhos-Pd6 (46.1 mg, 0.09 mmol), 2-(tributylstannyl)-pyrimidine (680 mg, 1.84 mmol) and N,N-dicyclohexylmethylamine (252 mg, 1.29 mmol) in DMF (5 mL) were heated at 100 C. for 48 hours. Then, the reaction mixture was cooled to room temperature, diluted with methylene chloride (100 ml), washed with water, dried through magnesium sulfate and evaporated to dry. The crude product was purified by column chromatography three times eluted with 20-100% ethyl acetate in hexane, 0-100% CAN in chloroform and 0-5% methanol in methylene chloride to afford the title compound as a yellow solid (26 mg, 8.5%). 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 8.93 (d, J=4.9 Hz, 2 H) 7.96 (t, J=7.2 Hz, 2 H) 7.56 (dd, J=8.2, 7.3 Hz, 1 H) 7.33 (t, J=5.0 Hz, 1 H) 6.41 (br. s., 2 H) 4.90 (quintet, J=8.7 Hz, 1 H) 4.46 (s, 2 H) 2.19-2.30 (m, 4 H) 1.71-1.83 (m, 2 H). MS APCI, m/z=332.3 (M+H). HPLC 1.63 min.

The synthetic route of 153435-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1421372-94-2 ,Some common heterocyclic compound, 1421372-94-2, molecular formula is C20H16FN5O3, 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.

Compound 6 (7.7 mL) was added to a suspension of N-(4-fluoro-2-methoxy-5 -nitrophenyl)-4-( 1- methylindol-3 -yl)pyrimidin-2-amine (compound 5, 15.5 g, 0.79) and K2C03 (16.3 g) in DMF (60 mL). The mixture was heated at 60 C for 60 mm and then water (150 mL) was added. Solids were filtered and rinsed with water. The crude dark red product was directly used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1421372-94-2, its application will become more common.

Reference:
Patent; NEUFORM PHARMACEUTICALS, INC.; CHAORAN, Huang; CHANGFU, Cheng; (85 pag.)WO2017/117070; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C13H19BrN4O2

To a stirred solution of tert-butyl-4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (15.0 g, 43.7 mmol) in 1,4-dioxane (50 mL), HCI in dioxane (150 mL, 10V, 4N) was added at 0 C and stirred at rt for 4 h. The resulting white precipitate was filtered and was washed with Et2O (25 mL), EtOAc (2 x 20 mL) to afford the title product. Yield: 98.2% (12.0 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 9.40 (br s, 2H), 8.54 (s, 2H), 3.93 (t, J = 4.8 Hz, 4H), 3.13 (br s, 4H). LCMS: (Method A) 244.9 (M -35), Rt. 1.71 min, 99.8 % (Max).

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

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.635698-56-5, name is tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, molecular formula is C12H15Cl2N3O2, molecular weight is 304.17, as common compound, the synthetic route is as follows.Formula: C12H15Cl2N3O2

To the mixture of tert-butyl 2,4-dichloro-7, 8-dihydropyrido[4,3 -d]pyrimidine6(5H)-carboxylate (4.00 g, 13.15 mmol) in CH2C12 (15.00 mL) was added HC1/dioxane (4 N,15.00 mL). The mixture was stirred at 15 C for 15 h. LCMS showed one main peak of desired product and about 5% of starting material. The mixture was stirred at 30 C for 1 h. LCMS showed desired product was major. The mixture was concentrated under reduced pressure to afford the title compound (3.07 g, crude, HC1 salt) as a white solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,635698-56-5, tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (2016); 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. 58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine, molecular formula is C22H15BrN2, 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. category: pyrimidines

Add intermediate IF-1 (12.18g, 31.45mmol) to a 250mL three-necked flask containing THF (100mL), and add n-butyllithium (1.99g, 31.09mmol) dropwise at -78 C. After the dropwise addition, the temperature is maintained for 1h. Trimethyl borate (4.61 g, 44.42 mmol) was then added dropwise, and the temperature was kept at room temperature for 1 h, followed by stirring overnight; hydrochloric acid (2 mol / L) was added to adjust the pH to neutral,After filtration, a white crude product was obtained, which was slurried with n-heptane to obtain a white solid intermediate I-F (7.68 g, yield 70%).

With the rapid development of chemical substances, we look forward to future research findings about 58536-46-2.

Reference:
Patent; Shanxi Laite Optoelectric Materials Co., Ltd.; Ma Tiantian; Yang Min; Nan Peng; (69 pag.)CN110615759; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia