Category: 6299-85-0

Electric Literature of 6299-85-0 , The common heterocyclic compound, 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, 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 Compound 8 (1.04 g, 5.0 mmol) and DIPEA (1.04 mL) in THF (5 mL) at 0 C. was added Compound 132 (0.92 g, 5.5 mmol). The mixture was warmed to RT and stirred overnight. The mixture was concentrated, diluted with water and extracted with EtOAc. The organic extracts were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SiO2, 0-80% EtOAc/DCM) to give Compound 133 as a white solid (1.5 g). Yield 89%. LC/MS: m/z=338 [M+H]+ (Calc: 337).

The synthetic route of 6299-85-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Purdue Pharma L.P.; Lynch, Stephen M.; Yao, Jiangchao; Park, Jae Hyun; Tafesse, Laykea; US2015/284383; (2015); 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. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, 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

General procedure: To a solution of nitrogen-containing nucleophile (1 eq.) and cesium carbonate (3.0 eq.) in N,N-dimethylformamide (2 mL/mmol) was added 2-haloheterocycle (1.1 eq.). Thereaction was heated to 100 C. and stirred at this temperature for 2 hours. Thereaction was then cooled to room temperature and acidified to pH=1 with 10%aqueous HCl solution if product contains a carboxylic acid, or diluted withwater if neutral. The solution was extracted with twice with dichloromethane.The organic layers were combined, dried with sodium sulfate and concentratedunder vacuum. The crude material was either used directly in subsequentreactions or purified by flash chromatography.

With the rapid development of chemical substances, we look forward to future research findings about 6299-85-0.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate, 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, COA of Formula: C6H4Cl2N2O2, blongs to pyrimidines compound. COA of Formula: C6H4Cl2N2O2

(1) To a solution of methyl 2,4-dichloropyrimidine-6-carboxylate (1.00 g, 4.83 mmol) and triethylamine (0.940 mL, 6.76 mmol) in N,N-dimethylformamide (6.0 mL) was added 4-aminotetrahydro-2H-pyran (537 mg, 5.31 mmol) at 0 C. After being stirred for 3.5 hour at 0 C., the reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:2) to give methyl 2-chloro-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-4-carboxylate as a colorless solid (1.12 g, 85%). mp 190-192 C. MS (APCI): m/z 272/274 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Kawanishi, Eiji; Matsumura, Takehiko; US2011/160206; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, the common compound, a new synthetic route is introduced below. SDS of cas: 6299-85-0

Intermediate C5; 2-Chloro-6-(piperidin-4-ylamino)-pyrimidine-4-carboxylic acid methyl ester dihydrochloride; Step 1: 6-( l-tert-Butoxycarbonyl-piperidin-4-ylamino)-2-chloro-pyrimidine-4-carboxylic acid methyl ester; A mixture of 2,6-dichloro-pyrimidine-4-carboxylic acid methyl ester (3.98 g, 19.19 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-l-carboxylic acid tert- butyl ester (5.0 g, 24.94 mmol, 1.3 equiv) in anhydrous DMF ( 100 mL) was heated to 60 0C for 18 h. The organic phase was concentrated under reduced pressure and the crude reaction mixture extracted from a 1 M NaOH ( 100 mL) solution with ethyl acetate (3 x 50 mL). The combined organic phases were dried over MgStheta4 and the product purified with silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ ethyl acetate providing 3.46 g (49%) of the title compound. 1H NMR (300 MHz, CDCl3): delta 1.42-1.51 (m, 2H), 1.47 (s, 9H), 2.00- 2.05 (m, 2H), 2.90-3.01 (m, 2H), 3.92 (s, 3H), 4.05-4.10 (m, 2H), 4.19 (br s, IH), 7.10 (s, IH), 7.17 (br s, IH). 13C NMR (75 MHz, CDCl3): (528.30, 31.23, 42.41, 48.00, 52.88, 79.61, 106.38, 153.58, 154.61, 161.21, 163.75, 164.23. MS (ISP): 371.1 [M+H]+.

The synthetic route of 6299-85-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/692; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 6299-85-0, 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.6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, molecular weight is 207.0142, as common compound, the synthetic route is as follows.

Methyl 2,6-dichloropyrimidine-4-carboxylate (150 mg, 725 pmol) and [4-(trifluoromethyl)phenyl]boronic acid (124 mg, 652 pmol) were dissolved in 3 ml. dioxane, aqueous sodium carbonate solution (1.1 ml_, 2.0 M, 2.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (83.7 mg, 72.5 pmol) were added. The mixture was stirred for 2h at 90C. The reaction mixture was filtered and the precipitate was washed with DCM to give the title compound as a salt ( 350 mg, 0.69 mmol, 60% purity). LC-MS (Method 1 ): Rt = 0.69 min; MS (ESIneg): m/z = 301 [M-H]

The chemical industry reduces the impact on the environment during synthesis 6299-85-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM; LEFRANC, Julien; SCHMEES, Norbert; ROeHN, Ulrike; ZORN, Ludwig; GUeNTHER, Judith; GUTCHER, Ilona; ROeSE, Lars; BADER, Benjamin; STOeCKIGT, Detlef; PLATTEN, Michael; (122 pag.)WO2019/101641; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 6299-85-0, 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. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, 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.

To a solution of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methanesulfonamide (0.875 g, 4.18 mmol) in DMF (25 mL) was added 60% NaH in mineral oil (0.193 g, 4.83 mmol). After 10 minutes, methyl 2,6-dichloropyrimidine-4-carboxylate (0.871 g, 4.21 mmol) was added. After stirring for 30 minutes, the reaction mixture was diluted into 100 mL water and extracted three times with 50 mL EtOAc. The combined organic layers were washed once with 25 mL brine, dried over MgSO4,filtered, and evaporated to a residue. The residue was chromatographed over silica gel with 30-60% EtOAc in hexanes. The product fractions were concentrated in vacuo. After sitting overnight a crystalline solid formed. The solid was decanted and dried under vacuum to give methyl 2-chloro-6-(N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methylsulfonamido)pyrimidine-4-carboxylate as a cream-colored powder (0.911 g, 2.40 mmol, 57% yield). LC/MS: m/z= 380.2 [M+H]+.

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 6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate.

Reference:
Patent; PURDUE PHARMA L.P.; LOCKMAN, Jeffrey; NI, Chiyou; PARK, Jae Hyun; PARK, Minnie; SHAO, Bin; TAFESSE, Laykea; YAO, Jiangchao; YOUNGMAN, Mark, A.; WO2014/135955; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 6299-85-0, 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. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Preparation of compound 47a: methyl 2-chloro-6-cyclopropylpyrimidine-4- carboxylateIn a 5 mL glass microwave tube methyl 2,4-dichloropyrimidine-6-carboxylate (621 mg, 3.00 mmol) (Astatech Inc.) and Amphos (53.1 mg, 0.075 mmol) were treated with cyclopropylzinc(II) bromide (Rieke, 0.5 M in THF) (1.2 mL, 6.00 mmol) via syringe under an atmosphere of argon. The solution was then heated in the microwave at 80 C for 20 min. The mixture was treated with EtOAc and IN NaOH resulting in a white suspension as the zinc hydroxide salts precipitated out. The suspension was extracted with EtOAc (50 mL) a second time and washed with brine and dried over Na2S04, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 100% DCM) to give methyl 2-chloro-6-cyclopropylpyrimidine-4-carboxylate (254 mg, 40% ) as a clear, colorless, viscous oil. MS (ESI, pos. ion) m/z: 213.1 (M+l). .H NMR (400 MHz, CDCh) delta ppm 7.77 (1 H, s), 3.99 – 4.04 (3 H, m), 2.06 – 2.15 (1 H, m), 1.20 – 1.31 (4 H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6299-85-0, its application will become more common.

Reference:
Patent; AMGEN INC.; WANG, Hui-Ling; CEE, Victor, C.; HERBERICH, Bradley, J.; JACKSON, Claire, L., M.; LANMAN, Brian, Alan; NIXEY, Thomas; PETTUS, Liping, H.; REED, Anthony, B.; WU, Bin; WURZ, Ryan; TASKER, Andrew; WO2012/129338; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6299-85-0, 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. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, 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.

Methyl 2,6-dichloropyrimidine-4-carboxylate (1.00 g, 4.83 mmol) and [4- (trifluoromethoxy)phenyl]boronic acid (895 mg, 4.35 mmol) were dissolved in 20 ml. dioxane, sodium carbonate (7.2 ml_, 2.0 M, 14 mmol) and tetrakis(triphenylphosphine)palladium(0) (558 mg, 483 pmol) were added. The mixture was stirred for 2h at 90C. The reaction mixture was filtered and the precipitate was washed with DCM to give the title compound as a salt (2.47 g, 4.65 mmol, 60% purity).LC-MS (Method 1 ): Rt = 0.71 min; MS (ESIpos): m/z = 319 [M+H]+H-NMR (400MHz, DMSO-d6): d [ppm]= 7.57 (dd, 2H), 8.35 – 8.44 (m, 2H), 8.54 (s, 1 H)2-Chloro-6-[4-(trifluoromethoxy)phenyl]pyrimidine-4-carboxylic acid (1 1.2 g, 66 % purity, 23.2 mmol) and (3-fluorophenyl)boronic acid (4.88 g, 34.8 mmol) were solubilised in 1 ,4-dioxane (170 ml) and aqueous sodium carbonate (35 ml, 2.0 M, 70 mmol) was added. The reaction mixture was sparged with argon and palladiumtetrakis (2.68 g, 2.32 mmol) was added. The mixture was stirred for 5h at 80C. The mixture was evaporated and the residue was stirred in HCI (1 M) overnight and the solid was filtered, washed with water and dried under reduced pressure at 60C. The solid was then stirred in DCM/EtOH overnight, filtered, washed with DCM and dried under reduced pressure to give 3.89 g (98 % purity, 43 % yield) of the title compound that was used without further purification.LC-MS (method 2): Rt = 1.42 min; MS (ESIneg): m/z = 377 [M-H]1H-NMR (400MHz, DMSO-d6): d [ppm]= 7.35 – 7.42 (m, 1 H), 7.55 (d, 2H), 7.61 (td, 1 H), 8.1 1 (s, 1 H), 8.23 – 8.29 (m, 1 H), 8.36 – 8.41 (m, 1 H), 8.43 – 8.49 (m, 2H).

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 6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM; LEFRANC, Julien; SCHMEES, Norbert; ROeHN, Ulrike; ZORN, Ludwig; GUeNTHER, Judith; GUTCHER, Ilona; ROeSE, Lars; BADER, Benjamin; STOeCKIGT, Detlef; PLATTEN, Michael; (111 pag.)WO2019/101647; (2019); 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 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Methyl 2,6-dichloropyrimidine-4-carboxylate

a) Methyl 2-chloro-6-(4-hydroxy-4-methyl-piperidin-1-yl)-pyrimidine-4-carboxylate; A mixture of methyl 2,4-dichloropyrimidine-6-carboxylate (1.66 g, 8.0 mmol), 4-methyl-piperidin-4-ol (1.21 g, 8 mmol) and sodium carbonate (1.74 g, 16.0 mmol) in methanol (8 mL) was stirred for 1 h at. The mixture was partitioned between ethyl acetate and water, and the organic layer was subsequently washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give crude title compound (1.70 g, 72%) as light yellow solid. MS ISP (m/e): 286.1 [(M+H)+].

With the rapid development of chemical substances, we look forward to future research findings about 6299-85-0.

Reference:
Patent; Baumann, Karlheinz; Flohr, Alexander; Goetschi, Erwin; Jacobsen, Helmut; Jolidon, Synese; Luebbers, Thomas; US2009/215759; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 6299-85-0 ,Some common heterocyclic compound, 6299-85-0, molecular formula is C6H4Cl2N2O2, 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.

44Step 1. To a mixture of 256-dichloro-pyrimidine-4-carboxylic acid methyl ester [1 g, 4.83 mmol, Intermediate (54)] and N,N-diisopropylethylamine (1.27 mL, 7.25 mmol) in THF (16 mL) is added 2- (4-methoxyphenyl)-ethylamine (707 ?L, 4.83 mmol). The resulting mixture is stirred at ambient temperature for 20 hours and poured into 50 mL water and extracted three times with 40 mL ethyl acetate. The organic extracts are combined and washed with 20 mL brine, dried over magnesium sulfate, filtered and concentrated to afford a solid which is purified via flash column chromatography on silica gel (35 g) eluting with 5 to 50% EtOAc in heptane gradient to afford 2-chloro-6-|”2-(4- methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester [1 g, 64.5%, Intermediate (55)]. LCMS: Rx = 2.9 minutes, MS: 322 (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,6299-85-0, its application will become more common.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/44732; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia