Pyrimidines

Application of 1193-21-1, 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. 1193-21-1, name is 4,6-Dichloropyrimidine. A new synthetic method of this compound is introduced below.

(a) 4-Chloro-6-[4-(trifluoromethyl)phenyl]pyrimidine. To a 500-mL, round-bottomed flask was added 4,6-dichloropyrimidine (14 g, 95 mmol, Aldrich), 4-(trifluoromethyl)phenylboronic acid (6.0 g, 32 mmol, Aldrich), acetonitrile (95 mL) and 1 M aqueous solution of sodium carbonate (95 mL). The mixture was deoxygenated by sparging with N2 for 15 min, and Pd(PPh3)4 (1.9 g, 1.6 mmol, Strem) was added. The resulting yellow mixture was heated at 80 C. with stirring for 15 h. After allowing to cool to 25 C., the mixture was evaporated under reduced pressure. The residue was diluted with 10% aqueous solution of NaHCO3 and extracted with CH2Cl2. The combined extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (gradient: 1.5-10% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 259 [M+1].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1193-21-1, 4,6-Dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Doherty, Elizabeth M.; Katon, Jodie; Norman, Mark H.; Retz, Daniel M.; Wang, Xianghong; Bo, Yunxin Y.; Tamayo, Nuria; Nishimura, Nobuko; Liao, Hongyu; US2006/241296; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 89581-38-4, Methyl 5-bromopyrimidine-2-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, Quality Control of Methyl 5-bromopyrimidine-2-carboxylate, blongs to pyrimidines compound. Quality Control of Methyl 5-bromopyrimidine-2-carboxylate

To a mixture of methyl 5-bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol) and copper (I) cyanide (1.92 g, 21.4 mmol) in a 100 mL round bottom flask was added DMA (21 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 5 min. The reaction mixture was heated to 110 C for 2 d and cooled to room temperature. The reaction mixture was diluted with EtOAc and water and filtered through a glass frit (medium). The filtrate was transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4 x) and the combined organic extracts were washed with brine (1 x), dried over MgS04, filtered, concentrated to give a yellow oil. Purification by flash column chromatography on silica gel (80 g, 5% to 50% EtOAc in heptane) gave methyl 5-cyanopyrimidine-2-carboxylate (0.83 g, 5.08 mmol, 48 % yield) as a white solid. LC/MS (ESI) m/z = 164.0 (M+H). Calculated for C7H5N3O2 163.0

The synthetic route of 89581-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); A1;,
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Pyrimidine – Wikipedia

Reference of 33034-67-2, 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.33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

To a mixture was sodium hydride (9 mg, 60percent dispersion) in 5 ml of dimethylformamide was added 4-(5-cyano-7-isopropyl-l,3-benzoxazol-2-yl)-N-[(5-methyl-2-oxo-l,3-oxazolidin-5- yl)methyl]benzamide (31 mg, EXAMPLE 65) followed by 2-chloro-4-trifluoromethylpyrimidine (14 mg). The mixture was stirred at 700C for 1 h. Excess sodium hydride was quenched by addition of 1 ml of methanol. The sample was then purified via mass-directed HPLC on a Kromasil Cl 8 column eluting with a gradient of 10percent acetonitrile in water (0.01percent TFA) to 60percent acetonitrile in water (0.01percent TFA) providing the title compound (25 mg, 59percent).

Statistics shows that 33034-67-2 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-(trifluoromethyl)pyrimidine.

Reference:
Patent; MERCK & CO., INC.; WO2008/156718; (2008); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 874-14-6, 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 874-14-6 as follows.

General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10molpercent) and 1,10-phenanthroline (15 molpercent) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF wasdried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobilephase. After completion, the reaction mixture was cooled, and water (10 ml) wasadded. The resulting solution was then extracted with EtOAc (3 QUOTE &13;&10;&13;&10;12?”> &13;&10;&13;&10;12?”> 20 ml). TheEtOAc extract was washed with water (5 QUOTE &13;&10;&13;&10;12?”> &13;&10;&13;&10;12?”> 10 ml) and thenbrine (10 ml). The organic layer was dried with Na2SO4.Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography onsilica gel (EtOAc-Petroleum ether).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,874-14-6, its application will become more common.

Reference:
Article; Mondal, Biplab; Hazra, Somjit; Roy; Tetrahedron Letters; vol. 55; 5; (2015); p. 1077 – 1081;,
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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. 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, the common compound, a new synthetic route is introduced below. Computed Properties of C17H13N5O

1L three bottles to join4-amino-3- (4-phenoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine 20 g (66 mmol)S-1-tert-butoxycarbonyl-3-hydroxypiperidine (26.6 g, 132 mmol); triphenylphosphine (51.9 g, 198 mmol) was added to dry tetrahydrofuran (400 mL) and cooled to 5-10 C.Under nitrogen, 40 g (198 mmol) of diisopropyl azodicarboxylate was slowly added dropwise to the flask and the reaction was carried out at 30 C for 12 hours. The reaction solution was cooled to 0 to 10 C, and 20 g of 36% hydrochloric acid was added dropwise(198 mmol), and the temperature was raised to 40 C for 1 hour.Water was added, stirred, extracted three times with dichloromethane, and the aqueous phase was collected and washed with hydrogenSodium hydroxide solution to adjust the water phase into alkaline (pH> 10), precipitate solid, filter, collect solid, blast 50 baking 12 hours(4-phenoxyphenyl) -1- (piperidin-3-yl) -1H-pyrazolo (3,4-d) pyrimidin-4-amine (V) 22.4 g, molar yield 87.9%. (HPLC purity 99.6%; optical purity ?99.8%).

The synthetic route of 330786-24-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Biocompounds Pharmaceutical Inc.; Yang, Shiqiong; Li, Qian; Kang, Litao; (14 pag.)CN106008526; (2016); A;,
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Pyrimidine – Wikipedia

Related Products of 1439-09-4, 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.1439-09-4, name is 5-Bromo-4-methylpyrimidine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.

To a sealed tube was added bis(pinacolato)diboron (220 mg, 0.87 mmol), 5-bromo-4-methyl-pyrimidine (100 mg, 0.58 mmol), Pd(dppf)Cl2 (42 mg, 0.06 mmol), potassium acetate (170 mg, 1.73 mmol) and 1,4-dioxane (1.5 mL). The mixture was stirred at 90 C. for 2 hours. LCMS showed the reaction was finished. The reaction mixture was used in the next step directly. LCMS (ESI): [M+H]+=139.2.

The chemical industry reduces the impact on the environment during synthesis 1439-09-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
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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 157335-93-8, name is 4,6-Dimethylpyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

The product of step 6 (50 mg) was treated in the same fashion as in Example 8, Step 4, using CH2Cl2 (3 ml), HOBt (28 mg), DEC (40 mg), diisopropyl ethyl amine (42 mg) and 4,6-dimethyl 5-pyrimidine carboxylic acid (24 mg); the reaction was stirred at RT for 2 days. Using the procedure described in Example 8, Step 4, the HCl salt of the title compound was prepared (59 mg) in 91% yield (from the product of Step 5). M.p:187-196 C. HRMS: calc’d: M-H+: C33H40ON5F3:580.3263; measured:580.3263.

With the rapid development of chemical substances, we look forward to future research findings about 157335-93-8.

Reference:
Patent; Schering Corporation; US6391865; (2002); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1194-78-1, 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 1194-78-1 as follows.

(D) 7-Chloro-1H-1,2,3-triazolo[4,5-d]pyrimidin-5-amine A solution of 6-chloro-2,4,5-pyrimidinetriamine (10.94 g, 0.0686 mol) and isoamyl nitrite (9.20 ml, 0.0686 mol)in dioxane (500 ml, freshly purified by passage through basic alumina) was heated under nitrogen with stirring for 2 hours at 90. The reaction mixture was cooled, treated with activated carbon, filtered, and concentrated to 150 ml. Petroleum ether (250 ml, bp 35-60) was added. The precipitate was filtered, washed the petroleum ether (50 ml) and dried in vacuo over P2 O5 at 40 for 16 hours to give 9.23 g of crude desired product which was then used in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1194-78-1, its application will become more common.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5126345; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1, 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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, 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.

Into a round bottom flask the catalyst PdCl2(dppf), under an atmosphere of nitrogen, was placed with 15 mL of toluene along with a stir bar. A suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 1.47 g, 9.57 mmol) in 15 mL of toluene was added at room temperature. After stirring for 10 minutes, methylmagnesium bromide (17.00 mL, 3.00 M in ether, 51.00 mmol) was added dropwise. The solution turned from orange to yellow, and was slowly heated to 60 C. and stirred for 3 hrs at 60 C. and then overnight at room temperature. The resulting dark orange reaction mixture was quenched with 1 N hydrochloric acid and adjusted to pH~5, then extracted with ethyl acetate and water saturated with sodium chloride. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluding with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a yellow solid (42, 202 mg). 1H-NMR(dmso-d6) was consistent with the desired compound. MS(ESI) [M+H+]+=134.3.

According to the analysis of related databases, 3680-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Plexxikon, Inc.; US2009/286783; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 54326-16-8 , The common heterocyclic compound, 54326-16-8, name is 5-Chloropyrimidin-2(1H)-one, molecular formula is C4H3ClN2O, 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.

EXAMPLE 25 5-Chloro-1-(4-cyanophenacyl)pyrimidin-2-one A suspension of 5-chloropyrimidin-2-one (412 mg) and 2-bromo-4′-cyanoacetophenone (677 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for one hour. Water (100 ml) was added and the collected solid was crystallized from ethyl acetate to give the title pyrimidinone (375 mg,); m.p. 236-240; lambdamaxEtOH 248 nm (epsilon 26140), 289 nm (epsilon 2130), lambdainf 254 (epsilon 22800).

The synthetic route of 54326-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; US4636509; (1987); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia