Day: July 19, 2021

Adding a certain compound to certain chemical reactions, such as: 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, 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, Quality Control of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, blongs to pyrimidines compound. Quality Control of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Example 4.Preparation of the isoamyl alcohol solvate (SI) of dasatinib:The intermediate of formula II (0.42 g; 1.07 mmol), l-(2-hydroxyethyl)piperazine (0.8 g; 6.15mmol) and diisopropylethylamine (0.38 ml, 2.18 mmol) were suspended in isoamyl alcohol (7ml) under an inert atmosphere. The reaction mixture was stirred and heated up to 140C for 6hours. The reaction mixture was withdrawn from the heating bath and stirred intensively. Crystallization started at the inner temperature of 95C, the suspension was left to cool under continuous stirring. After achieving the laboratory temperature it was stirred for another 2 hours. The crystalline substance was aspirated on fit S3, washed with isoamyl alcohol (7 nil)and dried at the laboratory temperature in vacuo (2.5 kPa) for 5 hours. The yield was 0.5 g;81% of the theoretical yield. FIPLC purity 99.10%. The XRPD pattern corresponds to the isoamyl alcohol solvate (SI). The SI solvate is characterized by the reflections presented in Table 2:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ZENTIVA, K.S.; ZELENKA, Karel; HAJICEK, Josef; DAMMER, Ondrej; WO2014/86326; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 14394-70-8, 2-Chloro-5-methylpyrimidin-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, 14394-70-8, blongs to pyrimidines compound. Formula: C5H6ClN3

[0293] A mixture of l-bromo-3,5-dimethoxybenzene (436 mg, 2.01 mmol), 2-chloro~5- methyl-pyrimidin-4-ylamine (287 mg, 2.00 mmol), Pd(OAc)2 (44 mg, 0.20 mmol), Xantphos (237 mg, 0.41 mmol) and potassium fe/t-butoxide (448 mg, 3.99 mmol) in dioxane (15 mL) and DMF (5 mL) was microwaved at 160 C for 20 min. The reaction mixture was cooled to room temperature and filtered rinsing with DCM and methanol. The filtrate was concentrated and purified using gradient flash chromatography (0-100% ethyl acetate in hexanes) to afford the title compound as a yellow solid (182 mg, 33%).[0294] 1H NMR (500 MHz, DMSO-d6): delta 2.17 (s, 3H), 3.74 (s, 6H), 6.27 (t, J= 2.2 Hz, IH), 6.99 (d, J=2.2 Hz, 2H), 8.06 (s, IH), 8.71 (s, IH). MS (ES+): m/z 280 (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: 64224-60-8, 5-Bromo-4-pyrimidinecarboxylic acid, 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, 64224-60-8, blongs to pyrimidines compound. SDS of cas: 64224-60-8

5-bromopyrimidine-4-carboxylic acid (prepared according to the procedure described in U.S. Pat. No. 4,110,450) (1.0 eq, 6.14 g, 30.2 mmol) was suspended in CH2Cl2 (100 ml). Oxalylchloride (1.1 eq, 2.9 ml, 33.0 mmol) was added followed by 2 drops of DMF. The mixture was stirred at room temperature overnight and the volatiles were removed in vacuo. The residue was taken in MeOH (50 ml) and heated. After evaporation of MeOH in vacuo the compound was dissolved in CH2Cl2 and poured on a prepacked silica gel column. The material was eluted using 20% Ethyl acetate in hexanes. Evaporation of the solvent provided methyl-5-bromopyrimidine-4-carboxylate as a light orange crystalline solid (2.54 g, 39% yield). LCMS (ES): 95% pure, m/z 217 [M]+; 219 [M+2]+; 1H NMR (CDCl3, 400 MHz) delta 4.04 (s, 3H), 9.02 (s, 1H), 9.21 (s, 1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64224-60-8, its application will become more common.

Reference:
Patent; CHUA, Peter C.; Haddach, Mustapha; Nagasawa, Johnny Y.; Pierre, Fabrice; Whitten, Jeffrey P.; US2009/239859; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3764-01-0, 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. 3764-01-0, name is 2,4,6-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

A solution of iotaetaomicronphietaomicronetabeta (100 g; 1.15 moles; 5.3 equivalents) in THF (450 mL) was cooled with an ice bath. A solution of 2,4,6-trichloropyrimidine (39.9 g; 217 mmoles; 1.0 equivalents) in THF (100 mL) was added over a period of 30 minutes. A copious white precipitate formed upon addition of 2,4,6-trichloropyrimidine and the reaction mixture rapidly thickened. The mixture was allowed to warm to ambient temperature and mechanically stirred for 64 hours (heating the reaction mixture at reflux following the addition of 2,4,6-trichloropyrimidine leads to complete reaction in 60 min. The ratio of a to b was unchanged). The mixture was then filtered and the filter cake washed with additional THF (2 x 100 mL). The filtrate was concentrated on the rotavap. Water (600 mL) was added and the resulting slurry was stirred for 30 minutes. The solids were isolated by filtration, washed with additional water (2 x 100 mL) and dried overnight under vacuum. Yield a + b: 61.3 g (99%). Product was 87% a by hplc area percent; remainder is b.[00128] 31 g of the crude solid was dissolved in 200 mL of CH2CI2 and applied to 600 g of dry silica in a fritted glass funnel. The silica was eluted with 1 : 1 hexane : EtOAc and 300 mL fractions were collected. TLC analysis shows a to be present in fractions 1 -7 and 4,6- dimo holino-2-chloropyrimidine in fractions 6-10. Fractions 1-5 were pooled and concentrated to provide a white solid. Yield: 28.2 g (Product was 98% a by hplc area percent).

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); 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.74356-36-8, name is 2,4-Dimethyl-pyrimidine-5-carboxylic acid, molecular formula is C7H8N2O2, molecular weight is 152.1506, as common compound, the synthetic route is as follows.Quality Control of 2,4-Dimethyl-pyrimidine-5-carboxylic acid

110 mg (0.72 mmol) of 2,4-dimethyl-pyrimidine-5-carboxylic acid and 215 mg (0.57 mmol) of O-(benzotriazol-1-yl)N,N,N’,N’-tetramethyluronium-hexa-fluorophosphate are dissolved in 4 mL of N,N-dimethylformamide and 62 muL (0.57 mmol) of 4-methyl-morpholine are added. The mixture is stirred for 10 min and a solution of 170 mg (0.47 mmol) [(R)-1-piperidin-4-yl-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester and 102 muL (0.57 mmol) of di-iso-propylethylamine in 4 mL of N,N-dimethylformamide is added. The reaction mixture is stirred for 2 h at room temperature, and diluted with ethyl acetate. The organic layer is washed with brine, saturated sodium bicarbonate solution and brine, dried with sodium sulfate, filtered and concentrated in vacuo to yield the title compound. LC/MS (I) (5-95%, 5 min): rt 3.89 min; m/z 437, 493 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,74356-36-8, 2,4-Dimethyl-pyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Santhera Pharmaceuticals (Schweiz) AG; BIOVITRUM AB; EP2019099; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 504-17-6, 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.504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, molecular weight is 144.1518, as common compound, the synthetic route is as follows.

General procedure: A mixture of dimedone (0.140 g, 1 mmol), isatin (0.147 g, 1 mmol) and malononitrile (0.066 g, 1 mmol) was stirred in round bottom flask containing 5 mL of oxalic acid dihydrate:proline LTTM at room temperature for an appropriate time. After completion of the reaction, as indicated by TLC, 10 mL of water was added to the reaction mixture and the insoluble crude product was filtered off. The aqueous layer was evaporatedunder vacuumto recover the LTTM. The crude product was washed with distilled water(5 mL) and recrystallized from ethanol (10 mL).

Statistics shows that 504-17-6 is playing an increasingly important role. we look forward to future research findings about 4,6-Dihydroxy-2-mercaptopyrimidine.

Reference:
Article; Chandam, Dattatray R.; Mulik, Abhijeet G.; Patil, Dayanand R.; Deshmukh, Madhukar B.; Research on Chemical Intermediates; vol. 42; 2; (2016); p. 1411 – 1423;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6693-08-9, 2,4,6-Trichloro-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, 6693-08-9, blongs to pyrimidines compound. SDS of cas: 6693-08-9

Intermediate 64-(2,6-Dichloro-5-fluoropyrimidin-4-yl)morpholineA round-bottom flask was charged with 2,4,6-trichloro-5-fluoropyrimidine (WO200549033, 2.0 g, 10 mmol), in EtOH (100ml) and was cooled to -200C. Morpholine (0.95 g, 11 mmol) in EtOH (20 ml) was added drop-wise to the reaction mixture in the course of 1 hour. The reaction was stirred at -200C for 30 minutes and at room temperature overnight. Solvent was removed under reduced pressure and the residue was partitioned between DCM and H2O. Organic phase was concentrated under reduced pressure to give a solid. Recrystallization from EtOH afforded the title compound (1.75 g, 86%). 1U NMR (delta) 6.76 (s, IH), 3.69 (m, 8H). LCMS: 252 [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,6693-08-9, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/132502; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 26452-81-3, 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.26452-81-3, name is 4-Chloro-6-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.

A RBF containing 4-chloro-6-methoxypyrimidine (3.13 g, 21.62 mmol), 4-chloro-2- (tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (7.31 g, 21.62 mmol), Na2CCb (2.29 g, 21.62 mmol), DME (86 ml), EtOH (10.81 ml) and water (10.81 ml) was equipped with a condenser. The mixture was purged with Ar for several min then Pd(dppf)Cl2-CH2Cl2 adduct (1.77 g, 2.16 mmol) was added. The reaction was heated at 90 °C for 5 h. The reaction was cooled to rt, diluted with water and extracted with EtOAc. The organic layer was washed with brine, concentrated and purified by normal phase chromatography to give 4-chloro-2-(6-methoxypyrimidin-4-yl)aniline (2.86 g, 56.1 percent yield) as yellow solid. MS (ESI) m/z: 236.0 (M+H)+. NMR (500MHz, CDCh) delta 8.78 (d, J=l .1 Hz, IH), 7.49 (d,J=2.5 Hz, IH), 7.15 (dd, J=8.8, 2.5 Hz, IH), 6.99 (d, J=l . l Hz, IH), 6.67 (d, J=8.8 Hz, IH), 5.89 (br. s., 2H), 4.03 (s, 3H).

Statistics shows that 26452-81-3 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-6-methoxypyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHU, Yeheng; DILGER, Andrew K.; EWING, William R.; ORWAT, Michael J.; PINTO, Donald J.P.; (156 pag.)WO2017/19821; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 905587-44-2, Adding some certain compound to certain chemical reactions, such as: 905587-44-2, name is 1-(5-Fluoropyrimidin-2-yl)ethanone,molecular formula is C6H5FN2O, 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 905587-44-2.

Method 4; l-(5-Fluoropyrimidin-2-yr)ethanol; l-(5-Fluoropyrimidin-2-yl)ethanone (Method 5, 0.77 g) was dissolved in MeOH (15 ml), and the solution was cooled to 0 0C. NaBH4 (0.210 g, 5.55 mmol) was added. The mixture was stirred at room temperature for 1 hour and then partitioned between EtOAc and H2O. The organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated to give the title compound as a yellowish oil (0.79 g, 99%). 1H NMR (CDCl3) delta 8.65 (s, 2H), 5.20 (m, IH), 4.00 (br s, IH), 1.80 (d, 3H).

According to the analysis of related databases, 905587-44-2, the application of this compound in the production field has become more and more popular.

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

Synthetic Route of 42839-09-8, 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. 42839-09-8, name is 2-Pyrimidinemethanol. A new synthetic method of this compound is introduced below.

Step C: Ethyl 3-(pyrimidin-2-ylmethoxy)isonicotinate: A solution of triphenyl phosphine (14.29 g, 54.49 mmol, 1.20 equiv) in 150 ml THF was cooled to -15 C. DIAD was added via syringe (10.70 ml, 54.49 mmol, 1.20 equiv). The reaction mixture was and stirred 10 minutes at -15 C., then a solution of pyrimidin-2-ylmethanol (5.00 g, 45.41 mmol, 1.00 equiv) in 30 ml THF was added. After 10 minutes, a solution of ethyl 3-hydroxyisonicotinate (7.590 g, 45.41 mmol, 1.00 equiv) in 75 ml THF was added to the reaction mixture and the reaction mixture was allowed to warm to ambient temperature over 16 hours. The reaction was concentrated under reduced pressure and the residue was purified by silica gel chromatography to give the desired product as an oil (7.238 g, 61%). MS (APCI-pos) M+1=260.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,42839-09-8, 2-Pyrimidinemethanol, and friends who are interested can also refer to it.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia