Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 26452-81-3, 4-Chloro-6-methoxypyrimidine, 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 C5H5ClN2O, blongs to pyrimidines compound. Computed Properties of C5H5ClN2O

General procedure: To a 5 mL vial containing a stir bar, 3-(2-aminopyrimidin-5-yl)-6-cyclobutyl-2-fluorophenol (88 mg, 0.34 mmol) and 4-amino-6-chloropyrimidine (46 mg, 0.36 mmol) were added K2CO3 (70 mg, mg, 0.51 mmol), 18-crown-6 (9 mg, 0.03 mmol) and DMA (0.68 mL). The resultant mixture was stirred at 120¡ã Celsius for approximately 3 hours before cooling to room temperature and passing it through a syringe filter and subjecting the filtrate to FCC to afford the title compound (42 mg, 35percent). The title compound was prepared using conditions similar to those described in Example 164 heating for 3 hours at 120¡ã Celsius using Intermediate G and 6-chloro-4-pyrimidinyl methyl ether giving title compound and Example 205. MS (ESI): mass calcd. for C19H20FN5O2, 369.16; m/z found, 370.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.46-8.42 (m, 1H), 8.08 (d, J=1.5, 1H), 7.98 (s, 1H), 7.78-7.69 (m, 1H), 7.32-7.27 (m, 1H), 5.90 (s, 1H), 4.67 (s, 2H), 3.51 (s, 3H), 1.37 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26452-81-3, 4-Chloro-6-methoxypyrimidine, and friends who are interested can also refer to it.

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;,
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Pyrimidine – Wikipedia

Electric Literature of 110100-00-0, 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. 110100-00-0, name is 1-(2-Chloropyrimidin-5-yl)ethanone, molecular formula is C6H5ClN2O, 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.

1. In a microwave oven, 1.000 g (6.387 mmol) of 1- (2-chloropyrimidin-5-yl) ethanone,1.236g (7.664mmol) (1R, 2S) -2,6-dimethylindene-1-amineA mixture of 2.476 g (19.161 mmol) of N, N-diisopropylethylamine in 8.0 mL of 1,4-dioxane was heated at 140 C for 45 minutes.The solvent was removed under reduced pressure, water and dichloromethane were added to the mixture, and the aqueous phase was extracted twice with dichloromethane.The combined organic phases were dried over sodium sulfate, and the solvent was distilled off under reduced pressure. : 50)] purification residue,Yielded 1.630 g (85%)1- (2-{[(1R, 2S) -2,6-dimethyl-2,3-dihydro-1H-inden-1-yl] amino} pyrimidin-5-yl) ethanone.

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 110100-00-0, 1-(2-Chloropyrimidin-5-yl)ethanone.

Reference:
Patent; Baier Crop Science Co., Ltd.; Baier Corporation; H ¡¤zhankebi; E ¡¤busikatuo¡¤aersaikeer; K ¡¤maien; U ¡¤duole; H ¡¤ditelixi; E ¡¤jiaciweile; A ¡¤B¡¤maqiedila; C ¡¤H¡¤luoxinge; D ¡¤shimucile; (88 pag.)CN110461833; (2019); A;,
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Related Products of 106157-82-8 ,Some common heterocyclic compound, 106157-82-8, molecular formula is C6H7N3O, 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 11a: 1 -(2-aminopyrimidin-4-yl)ethanone oxime; To a suspension of 1 -(2-aminopyrimidin-4-yl)ethanone (3a) (4 g) in ethanol (70 mL) and water (14 mL) was added hydroxylamine hydrochloride (4.05 g) followed by sodium acetate (7.18 g) and the mixture was stirred at room temperature for one hour. After this time the reaction mixture was concentrated in vacuo, water was added and stirred for 15 minutes. The precipitate was collected by filtration and washed with water and dried in vacuo at 40C overnight to afford the title product (4.29 g) as a light yellow solid.

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. 106157-82-8, 1-(2-Aminopyrimidin-4-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. Organon; GROVE, Simon James Anthony; MORRISON, Angus John; JAMIESON, Craig; PALIN, Ronald; MACLEAN, John Kinnaird Ferguson; WO2011/76723; (2011); A1;,
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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 35265-82-8, name is 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine

[0151] To an acetic acid (15 mL) solution of 24-f (according to the synthesis procedure in the patent: WO 2007/023382A2) (992 mg, 4.6 mmol) and aluminum trichloride (1.23 g, 9.2 mmol) was slowly added a solution of bromine (0.72 mL,13.8 mmol) in acetic acid (5 mL) at room temperature. After dropwise addition, the reaction mixture was heated to 80Cand stirred for 6 hours. After cooling, the reaction mixture was poured into ethyl acetate (40 mL), washed with water (40mL), then 5% sodium thiosulfate solution (40 mL 3 2) to remove the color of bromine. The aqueous phase was extractedwith ethyl acetate (120 mL 3 2). The organic layers were combined and washed with saturated sodium bicarbonatesolution (100 mL) and saturated brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to givetitle compound 24-e (1.035 g, yield 76%) as a pale yellow solid. LC-MS (ESI): m/z 296.9 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 35265-82-8.

Reference:
Patent; Shanghai Yingli Science and Technology Co., Ltd; Shanghai Chemexplorer Co., Ltd.; XU, Zusheng; EP2860181; (2015); A1;,
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Application of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

EXAMPLE 111 -(1 H-Pyrazolof3.4-dlpyrimidin-4-yl)-piperidin-4-ylanriine11A. f1-(1/-/-Pyrazolof3,4-cnpyrimidin-4-yl)-piperidin-4-yll-carbamic acid ferf-butyl esterTo a solution of 4-chloro-1/-/-pyrazolo[3,4-d]pyrimidine (J. Amer. Chem. Soc. 1957, 79, 6407-6413) (59 mg, 0.38 mmol) in ethanol (2 ml) was added triethylamine (100 mul, 0.72 mmol) and 4-(N-Boc-amino)piperidine (134 mg, 0.67 mmol). The solution was heated at 80 0C for 3 hours, and then cooled to room temperature. The solution was evaporated to dryness and the residue purified by recrystallisation (isopropanol) to yield the product (32 mg, 26% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5399-92-8, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; WO2007/125321; (2007); A2;,
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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.1005-37-4, name is 6-Chloro-N4-methylpyrimidine-2,4-diamine, molecular formula is C5H7ClN4, molecular weight is 158.59, as common compound, the synthetic route is as follows.Product Details of 1005-37-4

Example 2596-(4-methoxy-2,3-dimethylphenyl)-4-N-methylpyrimidine-2,4-diamine.A mixture of 6-chloro-4-N-methylpyrimidine-2,4-diamine (24 mg, 0.15 mmol), (4- methoxy-2,3-dimethylphenyl)boronic acid (32 mg, 0.18 mmol), potassium carbonate (41 mg, 0.30 mmol) and tetrakis(triphenylphosphine)palladium (0) (9mg, 0.008 mmol) in 1 ,4-dioxane (3 mL) and water (1 mL) was heated in a sealed tube at 90C overnight. The reaction mixture was concentrated and purified by preparative H PLC. LCMS [M+H] 259.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1005-37-4, 6-Chloro-N4-methylpyrimidine-2,4-diamine, and friends who are interested can also refer to it.

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;,
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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 138274-14-3, name is 5-(Benzyloxy)-2-chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 138274-14-3

Sodium hydride (400 mg, 8.33 mmol) was suspended in toluene (10 mL), ethyl 2-hydroxyacetate (0.70 mL,7.40 mmol) was added and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added(M-30) (1.00 g, 4.53 mmol), and the mixture was stirred at 60C for 18 hr. The reaction mixture was allowed to cool,saturated ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic layerwas dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residuewas purified by silica gel column chromatography (n-hexane:ethyl acetate) to give compound (M-31) (yield 650 mg,50%) as a colorless oil

With the rapid development of chemical substances, we look forward to future research findings about 138274-14-3.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
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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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, 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. Computed Properties of C15H13ClN2O4

A slurry containing methyl (?)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (80.9g at 99%, 0.25mols), potassium carbonate (52.8g at 98%, 0.375mols) and 2- cyanophenol (33.6g at 97.5%, 0.275mols) in isopropyl acetate (13OmIs) was heated to approximately 6O0C. A solution of DABCO (0.28g, 0.0025mols) in isopropyl acetate (1 OmIs) was added. The mixture was heated to 8O0C and held at this temperature for 360 minutes. The isopropyl acetate was removed by vacuum distillation to a maximum temperature of 8O0C. Toluene (160ml) was added to the distillation residues, maintaining the temperature between 60-700C, followed by water (265mls) which had been heated to 6O0C, again maintaining the temperature between 60-700C. The mixture was stirred for 40 minutes at 8O0C and then settled and the lower aqueous phase separated. The toluene solution (229.8g) EPO contained methyl (E)-2- {2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl} -3- methoxyacrylate (41.2%w/w) 94.2% of theory.

With the rapid development of chemical substances, we look forward to future research findings about 131860-97-4.

Reference:
Patent; SYNGENTA LIMITED; WO2006/114572; (2006); A2;,
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Pyrimidine – Wikipedia

Application of 514854-13-8 , The common heterocyclic compound, 514854-13-8, name is 6-Ethyl-5-iodopyrimidine-2,4-diamine, molecular formula is C6H9IN4, 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: The alkyne (1.2 eq), iododiaminoethyl pyrimidine (1.0 eq) was dissolved in anhydrous DMF (0.15M) and sonicated under argon. Pd(PPh3)2Cl2 (0.1 eq), CuI (0.21 eq), Et3N (24 eq) were added and again sonicated under argon for 15 minutes. The reaction mixture was heated at 60 C for 12h under argon. The reaction mixture was then concentrated in vacuo before preabsorbing onto a mixture of amine and 25% cysteine preabsorbed silica gel (1:1 /wt) and filterted through a plug of silica gel with 5% MeOH/ CH2Cl2. The collected reaction mixture was concentrated in vacuo, and further purified by preparative HPLC to furnish the final product

The synthetic route of 514854-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lombardo; Dayanandan; Keshipeddy; Zhou; Si; Reeve; Alverson; Barney; Walker; Hoody; Priestley; Obach; Wright; Drug Metabolism and Disposition; vol. 47; 9; (2019); p. 995 – 1003;,
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Application of 51-20-7, 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. 51-20-7, name is 5-Bromouracil, molecular formula is C4H3BrN2O2, 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.

Intermediate II (R)-tert-butyl-4-(2^-dioxo-l,2J^-tetrahvdropyrimidin-5-yl)-2-methylpiperazine-l- carboxylate In a Biotage microwave vial, 5-bromopyrimidine-2,4(lH,3H)-dione (la) (24 g, 125.67 mmol, Aldrich) and (R)-tert-butyl 2-methylpiperazine-l-carboxylate (37.8 g, 188.50 mmol, Activate Scientific) were taken in pyridine (12 mL) and irradiated at 150 C for 90 min. Pyridine was removed under vacuum and residue was poured in water to get the suspension, which was filtered and vacuum dried to get solid of (R)-tert-butyl-4-(2,4- dioxo- 1 ,2,3,4-tetrahydropyrimidin-5-yl)-2-methylpiperazine- 1 -carboxylate (22.00 g, 56.4 %). Note: Reaction was done in 12 batches of 2 g each. All combined and work up was done. 1H NMR (300 MHz, DMSO- 6) delta ppm 1.19 (d, J=6.78 Hz, 3 H) 1.40 (s, 9 H) 2.30 (d, J=2.83 Hz, 1 H) 2.42 (dd, J=11.30, 3.58 Hz, 1 H) 2.93 – 3.22 (m, 3 H) 3.72 (d, J=13.19 Hz, 1 H) 4.12 (br. s., 1 H) 6.73 (d, J=4.71 Hz, 1 H) 10.51 (br. s., 1 H) 11.10 (s, 1 H) MS (ES+), (M+H)+ = 310.09 for Ci4H22N404.

According to the analysis of related databases, 51-20-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; HAMEED PEER MOHAMED, Shahul; PATIL, Vikas; MURUGAN, Kannan; VITHALRAO BELLALE, Eknath; RAICHURKAR, Anandkumar; LANDGE, Sudhir; PUTTUR, Jayashree; ROY CHOUDHURY, Nilanjana; SHANBHAG, Gajanan; KOUSHIK, Krishna; IYER, Pravin; KIRTHIKA SAMBANDAMURTHY, Vasan; SOLAPURE, Suresh; NARAYANAN, Shridhar; WO2015/165660; (2015); A1;,
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