Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 16234-10-9, Thieno[3,2-d]pyrimidin-4(3H)-one, 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, 16234-10-9, blongs to pyrimidines compound. Safety of Thieno[3,2-d]pyrimidin-4(3H)-one

Thieno[3,2-d]pyrimidin-4(3H)-one (12.5 g) was dissolved in acetic acid (52 mL), and bromine (13 mL) was added thereto. The reaction mixture was stirred at 120 C. for 12 hours in a hermetically sealed reactor. The reaction mixture was cooled to room temperature and distilled under reduced pressure to remove acetic acid. The reaction mixture was placed in ice water, and the solid thus obtained was filtered and washed with ether, and dried to obtain the title compound (7.8 g). [0172] 1H NMR (300 MHz, DMSO-d6): delta 12.75 (brs, 1H), 8.36 (s, 1H), 8.24 (s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16234-10-9, its application will become more common.

Reference:
Patent; HANMI PHARM. CO., LTD; Son, Jung Beom; Kim, Nam Du; Chang, Young Kil; Kim, Hee Cheol; Kim, Ji Sook; Jung, Young Hee; US2013/274268; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 302964-08-5, 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 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.

A suspension of intermediate 3 (90 g, 1 equivalent) in DMSO (630 ml, 7 volumes) was heated to 60-650C. To this solution, HEP (89 g, 3 equivalents) was added until the reaction mixture became clear. Heating was continued at the same temperature for 6 hours (reaction was monitored by TLC and HPLC). Then the reaction mixture was allowed to cool to 25- 300C and dichloromethane (1890 ml, 21 volumes) was added, followed by the addition of water (1800 ml, 20 volumes). The mixture was stirred for 1 hour until a white precipitate appeared. The white solid was separated by filtration and dried under suction for 15-20 minutes. The solid was dried in a vacuum oven at 60-650C for 8-12 hours. The white solid obtained weighed 125 g and had a purity (by HPLC) of 99.6%. The solid was determined by XRPD analysis to be dasatinib DCM solvate (see Figure 1).

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

Reference:
Patent; GENERICS [UK] LIMITED; MYLAN INDIA PRIVATE LIMITED; GORE, Vinayak Govind; PATKAR, Laxmikant; BAGUL, Amit; VIJAYKAR, Priyesh Surendra; EDAKE, Mahesh; WO2010/139979; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3934-20-1, 2,4-Dichloropyrimidine, 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, 3934-20-1, blongs to pyrimidines compound. HPLC of Formula: C4H2Cl2N2

To a solution of 2,4-dichloropyrimidine (149 mg, 1 mmol) in THF (5 mL), tetrakis (triphenylphosphine) palladium (23 mg, 2 mol%) and 0.5M solution of phenylzinc bromide (2.1 mL, 1.05 mmol) in THF were added. The reaction mixture was stirred at50 C for overnight. Then it was added saturated ammonium chloride solution and extracted with EtOAc twice. The organic layers were combined, washed with water and dried(MgS04). Evaporation of solvent gave a yellow residue which was purified by Prep. HPLC to afford a yellowish oil as 2-chloro-4-phenyl- pyrimidine to carry on. To a solution of intermediate 2 (20 mg, 0.039 mmol) in DMF (3 mL), NaH (3.9 mg of 60% dispersion in mineral oil, 0.0975 mmol) was added at0 C. The reaction mixture was then warmed to rt. and stirred for 1 hr. Then 2-chloro-4-phenyl- pyrimidine prepared above (18 mg as crude) was added. The reaction mixture was stirred at rt. for overnight. It was then quenched with water and extracted with EtOAc. The organic layer was separated, washed with brine and dried(MgS04). Evaporation of solvent gave yellowish oil which was then purified by Prep. HPLC to give a thick colorless oil as final product (Compound 335) as TFA salt. (5.5 mg, 18% yield) ‘H NMR (CD30D, 300 MHz) 0.92-1. 12 (m, 11 H). 1.25 (m, 2 H), 1.44 (dd, J=9. 2, 5.5 Hz,1 H), 1.89 (dd, J=8. 1,5. 5 Hz, 1H), 2.17-2. 37 (m, 2 H), 2.57 (m, 1 H), 2.95 (m,1 H), 3.52 (s, 3 H), 4.14 (m,1 H), 4.24-4. 38 (m, 2 H), 4.51 (m,1 H), 5.13 (d, J=10. 2 Hz,1 H), 5.31 (d, J=17. 2 Hz,1 H), 5.77 (m,1 H), 5.86 (s,1 H), 7.48-7. 60 (m,3 H), 7.66 (d, J=5.3 Hz, 1 H), 8.18 (m,2 H), 8.60 (d, J=5.1 Hz, 1 H). LC-MS (retention time: 1.947 min. ), MS m/z 669(MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3934-20-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99274; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 39906-04-2, 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. 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine, molecular formula is C5H5Cl2N3, 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.

As shown in step 10-v of Scheme 10, to a solution of 4,6-dichloro-2-methyl-pyrimidin-5-amine (14.04 g, 78.88 mmol) stirred in methanol-d4 (140.4 mL) was added formic acid-d2 (7.77 g, 161.7 mmol) and Pd black (765 mg, 7.19 mmol, wetted in methanol-d4), followed by triethylamine (16.36 g, 22.53 mL, 161.7 mmol). The reaction mixture was sealed in a tube and stirred at RT overnight. The mixture was then filtered and concentrated under reduced pressure. Et2O (250 mL) was added and the mixture stirred for 1 hour at RT. The resulting solids were filtered and washed with Et2O (*2). The filtrate was concentrated under reduced pressure to yield 4,6-dideutero-2-methyl-pyrimidin-5-amine (compound 2043, 5.65 g, 65% yield) as a light yellow solid: 1H NMR (300 MHz, DMSO-d6) delta 5.25 (s, 2H), 2.40 (s, 3H). This compound was used in subsequent steps without further purification.

According to the analysis of related databases, 39906-04-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Charifson, Paul S.; Cottrell, Kevin Michael; Deng, Hongbo; Duffy, John P.; Gao, Huai; Giroux, Simon; Green, Jeremy; Jackson, Katrina Lee; Kennedy, Joseph M.; Lauffer, David J.; Ledeboer, Mark Willem; Li, Pan; Maxwell, John Patrick; Morris, Mark A.; Pierce, Albert Charles; Waal, Nathan D.; Xu, Jinwang; US2013/281431; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1753-50-0 ,Some common heterocyclic compound, 1753-50-0, molecular formula is C5H2ClN3, 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 compound AO (0.8 g, 4.73 mmol) in Ethanol (10 mL), DIPEA (40 mL, 23.6 mmol) and 2-chloropyrimidine-5-carbonitrile (AF, 0.85 g, 6.15 mmol) were added and the reaction mixture was stirred at 90C for 8 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 10% EtOAc/hexane to afford compound AP (1.1 g, 85%) as a thick oil. LC-MS: m/z 273.05 [M+l]+.

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. 1753-50-0, 2-Chloropyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 26032-72-4, 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. 26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine. A new synthetic method of this compound is introduced below.

The respective dichloropyrimidine derivative 9 (75 mg) and 1.5 equivalents of 1-methylpiperazine are dissolved in DMF (2.00 mL). The reaction mixture is heated to 40 C and stirred for 18 hours. Subsequently, the solvent is removed under reduced pressure and the crude product is purified via column chromatography (SiO2, ethyl acetate / methanol = 3:1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26032-72-4, its application will become more common.

Reference:
Article; Hammer, Sebastian G.; Gobleder, Susanne; Naporra, Franziska; Wittmann, Hans-Joachim; Elz, Sigurd; Heinrich, Markus R.; Strasser, Andrea; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 292 – 300;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 38275-56-8, 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 38275-56-8 as follows.

Step 1 : 5-Chloropyrimidine-2-carbonitrile (CAS 38275-56-8, 10 g) and hydroxylamine hydrochloride (5.23 g) were combined in Ethanol (107 ml) and stirred for 5 min. Sodium hydroxide (1M in Water, 72.4 ml) was added at room temperature. The mixture was stirred for 35 min. The mixture was diluted with ice and water. The precipitated solid was collected by filtration, washed with cold water and dried to give 5-chloro-N’-hydroxypyrimidine-2- carboximidamide (10.14 g) as colorless solid. MS: m/z = 173.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,38275-56-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; OBST SANDER, Ulrike; PETERS, Jens-Uwe; WOLTERING, Thomas; (99 pag.)WO2016/150785; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 705263-10-1 ,Some common heterocyclic compound, 705263-10-1, molecular formula is C6H4BrN3, 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 solution of 6-bromopyrazolo[1,5-a]pyrimidine (S2, 1 equiv) in DMF/H2O (9:1, 10 vol) was added compound S1 (1 equiv), K2CO3(2 equiv), and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90 C. for 5 h and then concentrated. The remaining residue was purified by column chromatography on silica gel to give compound S3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,705263-10-1, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 14394-70-8 ,Some common heterocyclic compound, 14394-70-8, molecular formula is C5H6ClN3, 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.

[0152] A suspension of 2-chloro-5-methylpyrimidin-4-amine (159 muL, 1.2 mmol), 1- bromo-4-(trifluoromethyl)benzene (150 mg, 1.0 mmol), potassium tert-bntoxide (224 mg, 2.0 mmol), Xantphos (120 mg, 0.2 mmol), and palladium acetate (26 mg, 0.1 mmol) was sealed in a microwave reaction tube and irradiated at 160 C for 15 min. The mixture was allowed to cool to room temperature, the solids were filtered using DCM to rinse, and the solution was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (hexane to EtOAc) to afford the title intermediate 29 (128.7 mg, 43%) as a white solid. MS (ESI+): m/? 288 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14394-70-8, its application will become more common.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 14080-59-2, 4-Chlorothieno[2,3-d]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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Under argon atmosphere, 4-methylphenylboronic acid (4.8 g, 35 mmol) was added to a 250 mL round bottom flask.4-chlorothiophene [2,3-d]pyrimidine (5.1 g, 30 mmol),Pd(dppf)Cl2 (440 mg, 0.6 mmol),K2CO3 (5.5 g, 40 mmol),60mL 1,4-dioxane and 20mL water,The mixture was heated at 90 C with stirring for 6 h.Cool to room temperature, quench with water, extract with dichloromethane, and remove the solvent on a rotary evaporator.Purification by column chromatography. A white solid was obtained (4.5 g, 72%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14080-59-2, 4-Chlorothieno[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Wuhan University; Yang Chuluo; Jiang Bei; Ning Xiaowen; (32 pag.)CN107573386; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia