Pyrimidines

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. 39551-54-7, name is 2,4-Dichloropyrido[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below., Product Details of 39551-54-7

Compound 94j (195.7 mg, 0.798 mmol) was dissolved in 4M HCl in dioxane (3 mL) and stirred at rt for 1 h. The reaction mixture was then concentrated in vacuo. The residue was treated with 2-methyltetrahydrofuran (5 mL), 2,4-dichloropyrido[3,2-d]pyrimidine (160 mg, 0.525 mmol) and N,N-diisopropylethylamine (0.57 mL, 3.272 mmol) and heated with an 80 C. bath for 3 h. The reaction mixture was cooled to rt, concentrated under reduced pressure and the residue was subjected to silica gel chromatography eluting with 0-100% EtOAc in hexanes to obtain compound 96a as a mixture of two diastereomers (2:3 ratio). LCMS-ESI+ (m/z): [M+H]+ calculated for C15H22ClN4O: 309.15. found: 309.08; TR=1.41 min on LC/MS Method A.

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, 39551-54-7, 2,4-Dichloropyrido[3,2-d]pyrimidine.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Mackman, Richard L.; Metobo, Samuel E.; Mish, Michael R.; Pyun, Hyung-jung; Zablocki, Jeff; (175 pag.)US2016/289229; (2016); A1;,
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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.10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine, molecular formula is C8H9Cl2N3O, molecular weight is 234.08, as common compound, the synthetic route is as follows.Safety of 4-(4,6-Dichloropyrimidin-2-yl)morpholine

Step 1: A mixture of 2,2-dimethylmorpholine (2.0 equiv.), 4-(4,6-dichloropyrimidin-2-yl)morpholine (1 equiv.) and triethylamine (6 equiv.) in EtOH (0.2 M) were heated to 110 C. for 25 min in the microwave. The reaction mixture was partitioned between EtOAc and water. The organic phase was dried over sodium sulfate. The resulting solution was concentrated and dried under vacuo to give 4-(6-chloro-2-morpholinopyrimidin-4-yl)-2,2-dimethylmorpholine and was used in the next step without further purification. LCMS (m/z) (M+H)=313.2, Rt=0.86 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10397-13-4, 4-(4,6-Dichloropyrimidin-2-yl)morpholine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; Barsanti, Paul A.; Burger, Matthew; Lou, Yan; Nishiguchi, Gisele; Polyakov, Valery; Ramurthy, Savithri; Rico, Alice; Setti, Lina; Smith, Aaron; Taft, Benjamin; Tanner, Huw; DiPesa, Alan; Yusuff, Naeem; US2014/275003; (2014); A1;,
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Application of 257280-25-4, 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.257280-25-4, name is 5-Bromo-2-phenoxypyrimidine, molecular formula is C10H7BrN2O, molecular weight is 251.08, as common compound, the synthetic route is as follows.

Synthesis of 2-(2-chloro-6-fluorophenyl)-5-(2-phenoxypyrimidin-5-yl)- lH-imidazole-4-carbonitrile (EX-43)[000265] A solution of 5-bromo-2-phenoxypyrimidine (1-28) (0.3 mmol) and hexamethylditin (0.3 mmol) in DME (3 mL) was degassed with nitrogen for 5 minutes. Pd(PPh3 )4 (0.015 mmol) was added and the reaction was heated at 80 0C for 12 hours. The reaction was subsequently cooled to room temperature and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and reduced to dryness. The crude product was purified by flash column chromatography (hexanes : EtOAc = 9 : 1) to afford 5-(trimethylstannyl)-2-phenoxypyrimidine (1-29) as a clear oil. MS (m/z) (M+l)+: 335.0, 337.0. [000266] 5-(Trimethylstannyl)-2-phenoxypyrimidine (1-29) (0.16 mmol) and 5-bromo-2- (2-chloro-6-fluorophenyl)-lH-imidazole-4-carbonitrile (1-10) (0.083 mmol) were dissolved in DME (2 mL) and degassed for 5 minutes with nitrogen. Pd(PPh3)4 (0.0082 mmol) was added and the reaction was heated at 85 0C for 12 hours. The reaction was cooled to room temperature and partitioned with EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and reduced to dryness. The crude product was purified by flash column chromatography (hexanes : EtOAc = 3 : 1) to afford 2-(2-chloro-6- fluorophenyl)-5-(2-phenoxypyrimidin-5-yl)-lH-imidazole-4-carbonitrile (EX-43) as white glassy solid. 1U NMR (400MEtaz, d4-MeOO) delta 8.95 (s, 2H), 7.50 (m, IH), 7.37 (m, 3H), 7.21 (m, 2H), 7.14 (m, 2H). MS (m/z) (M+l)+: 392.5.

Statistics shows that 257280-25-4 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-phenoxypyrimidine.

Reference:
Patent; IRM LLC; CHIANELLI, Donatella; MOLTENI, Valentina; ALBAUGH, Pamela A.; CHOI, Ha-Soon; LOREN, Jon; WANG, Zhicheng; MISHRA, Pranab; WO2010/127152; (2010); A2;,
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Electric Literature of 58347-49-2, 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 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 15Ethyl (4- { 8 -chloro-3 – IY 1 S)- 1 -(pyrazolof 1 ,5 -a]pyrimidin-7-ylamino)ethyllquinolin-2- yl } piperazin- 1 – vDacetateIntermediate 22 (500 mg, 1.05 mmol), EtOH (5 mL) and 2N HCl in Et2O (5 mL) were combined and stirred at r.t. for 4 days. The reaction mixture was then concentrated to give a yellow glass (526 mg, quantitative). A portion of this material (50 mg, 0.11 mmol), «-BuOH (6 mL), DIPEA (1 mL) and 7-chloropyrazolo[l,5-alpha]pyrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated under microwave irradiation to 14O0C for 1 h. The reaction mixture was then concentrated and purified by preparative HPLC to give the title compound (39.3 mg, 72%) as a tan glass. deltaH (DMSOd6) 8.68 (IH, s), 8.47 (IH, d, J7.70 Hz), 8.14-8.09 (2H, m), 7.86-7.76 (2H, m), 7.40 (IH, t, J7.81 Hz), 6.44 (IH, d, J2.27 Hz), 6.26 (IH, d, J5.28 Hz), 5.14-5.05 (IH, m), 4.16 (2H, q, J7.10 Hz), 3.47-3.38 (2H, m), 3.42 (2H, s), 3.38-3.29 (2H, m), 3.00-2.93 (2H, m), 2.90-2.82 (2H, m), 1.90 (3H, d, J 6.69 Hz), 1.25 (3H, t, J 7.09 Hz). LCMS (ES+) 494/496 (M+H)+, RT 3.50 minutes {Method 1).

According to the analysis of related databases, 58347-49-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); A1;,
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Application of 171887-03-9, Adding some certain compound to certain chemical reactions, such as: 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide,molecular formula is C5H4Cl2N4O, 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 171887-03-9.

Example 25 Preparation of (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene 145.2 ml of a solution of (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene (preparation similar to that in Example 14) were concentrated to 25.5 ml and filtered through Celite. The filter cake was washed with 7.5 ml of water. The filtrate contained 17.7 mmol of the above compound (HPLC) and was adjusted from pH 6.6 to pH 1 with conc. HCl and then extracted 3 times with 20 ml of isobutanol. The organic phase was discarded. The aqueous phase was adjusted to pH 12 with 30% strength NaOH and extracted 3 times with 10 ml of isobutanol. The combined organic phases were evaporated to 15 ml and 2.53 g of triethylamine were added. A solution of 2.07 g of N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide in 40 ml of ethanol was added to the mixture as in Example 24. The mixture was stirred at 80 C. for 16 h. Working up as in Example 22 resulted in 2.4 g of title compound. The yield was 85%.

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. 171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lonza AG; US6137007; (2000); A;,
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Pyrimidine – Wikipedia

Related Products of 504-17-6 ,Some common heterocyclic compound, 504-17-6, molecular formula is C4H4N2O2S, 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: [H2-DABCO][H2PO4]2 (0.065mmol, 0.020 g) was added to a mixture of the aromatic aldehyde (1 mmol), malononitrile (1 mmol) and barbituric or thiobarbituric acid (1 mmol) in water (3 mL). Then the mixture was heated at 75 C while was monitored by TLC (n-hexane:ethyl acetate; 1:9). After completion of the reaction, the mixture was cooled to room temperature and the solid productwas filtered, washed with cold distilled water (2 mL) and was recrystallized from warm ethanol if necessary.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,504-17-6, its application will become more common.

Reference:
Article; Shirini, Farhad; Langarudi, Mohaddeseh Safarpoor Nikoo; Daneshvar, Nader; Journal of Molecular Liquids; vol. 234; (2017); p. 268 – 278;,
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Pyrimidine – Wikipedia

Application of 5018-38-2, Adding some certain compound to certain chemical reactions, such as: 5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine,molecular formula is C5H4Cl2N2O, 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 5018-38-2.

Example 9 4-chloro-5-methoxy-6-piperazin-1-yl-pyrimidine A modification of the process used by Smith et al. in EP 0464604 was used. To a solution of 21.5 g (0.25 mol) of piperazine in 150 ml of EtOH and 50 ml of water stirred vigorously at 25C were added 17.9 g (0.1 mol) of 4,6-dichloro-5-methoxypyrimidine. The reaction was held for 3 hours, with the temperature held to between 25-30C. At the end of this time, the reaction mixture was concentrated to dryness and to the residue was added 100 ml of a solution 1N NaOH followed by extraction with 3 x 100 ml of dichloromethane. The organic phase was dried and concentrated. The residue was purified by chromatography on silica gel, eluding with CH2Cl2/EtOH/NH4OH 70/25/5 thus to yield 19.2 g (83.9%) of a colourless oil which rapidly solidifies.

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. 5018-38-2, 4,6-Dichloro-5-methoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VITA-INVEST, S.A.; EP714896; (1996); A1;,
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Pyrimidine – Wikipedia

Reference of 25940-35-6, 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. 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

To a solution of 5-[6-(difluoromethoxy)-3,4-dihydro-2H-l-benzopyran-7-yl]-l-[[2- (trimethylsilyl)ethoxy]methyl]-lH-pyrazol-4-amine (154 mg, 0.374 mmol) in DMA (3.0 mL) was added pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (92.0 mg, 0.564 mmol), 4-DMAP (5.00 mg, 0.0409 mmol), DIPEA (145 mg, 1.12 mmol) and PyAOP (293 mg, 0.562 mmol). The reaction mixture was stirred at 45 C for 18 h. The reaction mixture was allowed to cool to RT and partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with ethyl acetate/petroleum ether (1/1) to afford N-[5-[6-(difiuoromethoxy)-3,4-dihydro-2H-l-benzopyran-7-yl]-l-[[2- (1224) (trimethylsilyl)ethoxy]methyl]- lH-pyrazol-4-yl]pyrazolo[ 1 ,5-a]pyrimidine-3-carboxamide (170 mg, 82%) as an off-white solid. LC/MS (Method F, ESI): [M+H]+ = 557, RT = 1.26 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,25940-35-6, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ROMERO, F. Anthony; ZAK, Mark; ZHAO, Guiling; GIBBONS, Paul; LI, Wei; CHENG, Yun-Xing; YUEN, Po-Wai; CHENG, Limin; (275 pag.)WO2018/122212; (2018); A1;,
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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. 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole, molecular formula is C13H10ClN3, 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. name: 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole

P-toluenesulfonic acid hydrate (43.25 g) was added in one portion to 3-(2-chloropyrimidin-4-yl)-1-methyl-oxime(Intermediate 4, 32.17g)And 4-fluoro-2-cyclopropylmethoxy-5-nitroaniline (intermediate 5, 24.14g)In a mixture of 2-pentanol (500 mL).The resulting mixture was stirred at 105 C for 2.5 hours.It was then cooled to room temperature.The resulting precipitate was collected by filtration, washed with 2-pentanol (50 mL), dried under vacuum to give some of the desired product as a yellow solid.The filtrate was cooled, and the obtained precipitate was collected by filtration and washed with 2-pentanol (10 mL).The two batches were combined and triturated with CH3CN to give a solid which was collected by filtration.Drying under vacuum gave the title compound in yield86%.

With the rapid development of chemical substances, we look forward to future research findings about 1032452-86-0.

Reference:
Patent; Jiao Yuqi; (26 pag.)CN108929311; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 39876-88-5, 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.39876-88-5, name is 4-Chlorobenzofuro[3,2-d]pyrimidine, molecular formula is C10H5ClN2O, molecular weight is 204.61, as common compound, the synthetic route is as follows.

A mixture of 4-chlorobenzofuro[3,2-djpyrimidine (1.01 g, 4.94 mmol) and (4-bromo-2-fluorophenyl)methanamine (1.04 g, 5.10 mmol) in acetonitrile (50 mL) in apressure bottle was treated with Hunig?s base (1.6 mL, 9.16 mmol) and the resulting suspension stirred at RT for 10 mm, then heated to 120 C in an oil bath. After 5 hours the mixture went into solution and was then stirred for 16 hours overnight. A pale yellow solid had formed while at 120 C, then the reaction mixture was cooled to RT. Themixture was filtered and washed with CH3CN, and was dried under vacuum to give 1.43 g (78%) ofN-(4-bromo-2-fluorobenzyl)benzofuro[3,2-djpyrimidin-4-amine as a pale yellow solid. LCMS (M+1) = 371.6/373.6.

The chemical industry reduces the impact on the environment during synthesis 39876-88-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
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