Day: June 18, 2021

Adding a certain compound to certain chemical reactions, such as: 2244-11-3, Pyrimidine-2,4,5,6(1H,3H)-tetraone hydrate, 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 C4H4N2O5, blongs to pyrimidines compound. Computed Properties of C4H4N2O5

General procedure: 0.5 mmol of alloxan monohydrate (0.08 g) and suitable methyl ketone were suspended in 5 mL of glacial acetic acid and reacted in a Syncore apparatus set at the temperature of 115 C, shaking at 120 rpm and reaction time 3 h. All the targeted compounds precipitated after cooling and were recrystallized from ethanol. Compounds 19 and 20 were obtained as a mixture in a 36:64 ratio (total yield 75%); chromatographic purification of the crude (gradient eluent: methanol in dichloromethane 0-10%) afforded the pure final compounds. 5.1.2.2 5-[2-(4′-Methylbiphen-4-yl)-2-oxoethyl]-5-hydroxy-hexahydropyrimidine-2,4,6-trione (8) 69% Yield, mp > 250 C 1H NMR delta 11.46 (s, 2H, NH), 8.02 (d, 2H, Jo = 8.7), 7.82 (d, 2H, Jo = 8.7), 7.65 (d, 2H, Jo = 8.4), 7.30 (d, 2H, Jo = 8.4), 7.31 (s, 1H, OH), 3.91 (s, 2H), 2.34 (s, 3H). Anal. % (C19H16N2O5) calculated: C 64.77, H 4.58, N 7.95; found C 64.56, H 4.60, N 7.82.

The synthetic route of 2244-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nicolotti, Orazio; Catto, Marco; Giangreco, Ilenia; Barletta, Maria; Leonetti, Francesco; Stefanachi, Angela; Pisani, Leonardo; Cellamare, Saverio; Tortorella, Paolo; Loiodice, Fulvio; Carotti, Angelo; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 368 – 376;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 18592-13-7 ,Some common heterocyclic compound, 18592-13-7, molecular formula is C5H5ClN2O2, 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.

Part A A mixture of 100 g (0.623 mole) of 6-chloromethylpyrimidine-2,4-dione and 200 ml of anhydrous ammonia was allowed to react overnight in a sealed bomb at about 20 C. The solid residue was slurried in ethyl acetate, and was then separated by filtration and washed sequentially with water and methanol to provide 6-aminomethylpyrimidine-2,4-dione, m.p. 295-297 C.

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. 18592-13-7, 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Riker Laboratories, Inc.; US4478835; (1984); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 38275-55-7, name is 5-Fluoropyrimidine-2-carbonitrile. A new synthetic method of this compound is introduced below., Computed Properties of C5H2FN3

To a mixture of 1-ethyl-7-fluoro-6-methoxy-1,2,3,4-tetrahydroisoquinoline (0.3 g, 1.43 mmol) and 5-fluoropyrimidine-2-carbonitrile (0.26 g, 2.15 mmol) in DMF (8 mL) was added cesium carbonate (1.4 g, 4.3 mmol) under N2. The mixture was stirred at 100 C for 12 hours. The reaction mixture was cooled to rt, diluted with H2O (30 mL) and extracted with EtOAc (3 x 30 mL). The combined organic phase was washed with saturated aqueous brine solution (30 mL), dried over anhydrous sulfate, filtered and concentrated in vacuum. The residue was purified via normal phase SiO2 chromatography (0-20% EtOAc/petroleum ether) to give 5-(1-ethyl-7-fluoro-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl) pyrimidine-2- carbonitrile as a yellow solid (0.2 g, 45% yield, m/z: 313 [M+H]+ observed). 1H NMR (400 MHz, CDCl3) d 8.31 (s, 2H), 6.89 (d, J = 10.8 Hz, 1H), 6.80 (d, J = 8 Hz, 1H), 4.54 (t, J = 7.6 Hz, 1H), 3.90 (s, 3H), 3.73-3.67 (m, 1H), 3.61-3.54 (m, 1H), 3.03 (t, J = 6 Hz, 2H), 2.00-1.93 (m, 1H), 1.81-1.74 (m, 1H), 1.01 (t, J = 7.6 Hz, 3H).

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, 38275-55-7, 5-Fluoropyrimidine-2-carbonitrile.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; COLE, Andrew G.; DORSEY, Bruce D.; DUGAN, Benjamin J.; FAN, Yi; GOTCHEV, Dimitar B.; KAKARLA, Ramesh; QUINTERO, Jorge; SOFIA, Michael J.; (220 pag.)WO2019/222238; (2019); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 155405-80-4, 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. 155405-80-4, name is Methyl 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoate, molecular formula is C16H16N4O3, 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.

The current synthetic route for the preparation of Pemetrexed IM8 starts with an aldol-condensation reaction of Methyl-4-formylbenzoate (SM1 ) with 1 ,1- Dimethoxyacetone (SM2) to give Pemetrexed IM1a. As Pemetrexed IM1a irreversibly converts to its aldol-addition product Pemetrexed IM1 b under reaction conditions the reaction mixture is directly submitted to hydrogenation (i.e. without isolation of Pemetrexed IM1a) over Pd/C to give Pemetrexed IM2. As under the hydrogenation conditions not only the double- bond of IM1a is hydrogenated but also some amount of Pemetrexed IM2 is converted to Pemetrexed IM3 (hydrogenation of the carbonyl function to the corresponding secondary alcohol) a solution of NaBH4 is added to the reaction mixture to ensure complete conversion to Pemetrexed IM3. The Pd- catalyst is removed by filtration and the reaction mixture is extracted with toluene. The combined organic layers are evaporated to give crude Pemetrexed IM3 as oil. This oil is dissolved in THF and the alcohol functionality is converted to a mesylate using MsCI and NEt3. The salts are removed by filtration, glacial acetic acid is added and THF is removed by distillation. Upon addition of water Pemetrexed IM4 crystallizes and is isolated by filtration. The dried Pemetrexed IM4 is dissolved in glacial acetic acid and gaseous HCI is added to cleave the dimethoxy acetale and liberate the aldehyde functionality of Pemetrexed IM5. Upon complete deprotection a solution of 2,6-diamino-4-hydroxypyrimidine in aq. NaOH and acetonitrile is added. Upon complete conversion the crystallized Pemetrexed IM6 is isolated by filtration. The saponification of the methyl ester of Pemetrexed IM6 to Pemetrexed IM7 is done using aqueous NaOH. Upon addition of aq. HCI first the Na-salt of Pemetrexed IM7 crystallizes from the reaction mixture. The salt is isolated by filtration, purified by slurry in a mixture of MeOH and water and then converted to Pemetrexed IM7 by pH adjustment in water using aq. HCI. Dried Pemetrexed IM7 (water content not more than 6.0%) is dissolved in DMF, activated using 1 ,1-carbonyldiimidazolide (CDI) and then reacted with dimethyl-L-glutamate hydrochlorid to give, upon addition of water and filtration, crude Pemetrexed IM8. This intermediate is purified by tosylate salt formation, followed by recrystallization and liberation to give pure Pemetrexed IM8. Starting with the saponification of Pemetrexed IM8 the preparation of different solid forms of Pemetrexed Disodium can be achieved. Methods for Preparing Pemetrexed Disodium Form IV and Investigation of its Stability

According to the analysis of related databases, 155405-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AZAD PHARMACEUTICAL INGREDIENTS AG; ALBRECHT, Uwe, Jens; HELMBOLDT, Hannes; NIKOLAEV, Vsevolod, Valiervich; WO2011/64256; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 58347-49-2, Adding some certain compound to certain chemical reactions, such as: 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine,molecular formula is C6H4ClN3, 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 58347-49-2.

A solution of 7-chloropyrazolo[l,5-ajpyrimidine (0.1 g, 0.651 mmol), 6-bromo-2-(difluoromethyl)-3 -fluoropyridine (0.162 g, 0.716 mmol) and 1,1,1,2,2,2-hexamethyldistannane (0.235 g, 0.7 16 mmol) in 1,4-dioxane (2 mL) was purged with nitrogen gas for 10 mi Pd(Ph3P)4 (0.075 g, 0.065 mmol) was added to the reaction mixture and the solution was purged with nitrogen gas for another 10 mm. The reaction mixture was heated at 150 C for 1.5 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue waspurified by silica-gel chromatography (pet ether/ethyl acetate (0-40%)) to afford 7- (6-(difluoromethyl)-5-fluoropyridin-2-yl) pyrazolo [1,5-al pyrimidine (40 mg, 0.151 mmol, 23% yield) as a yellow solid .LCMS (ESI) m/e 265.0 [(M+H), calcd for C12H8F3N4 265.11; LC/MS retention time (Method Al): tR = 2.08 mm.

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; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 165807-05-6, 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.165807-05-6, name is 4-Dimethoxymethylpyrimidin-2-ylamine, molecular formula is C7H11N3O2, molecular weight is 169.18, as common compound, the synthetic route is as follows.

Intermediate P: 1-(4-((2-Aminopyrimidin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureaHydrochloric acid (2M, 207 mL, 414 mmol) was added to 4-(dimethoxymethyl)pyrimidin-2-amine (68) (WO 2007/096764) (14.0 g, 83 mmol) and the mixture heated at 48° C. for 16 hr.The mixture was cooled to RT and was neutralized with solid Na2CO3 which produced a precipitate at pH 7.The suspension was diluted with EtOAc (300 mL) and the solid removed by filtration.The organic layer was separated and the aqueous layer was extracted with 1percent MeOH in THF (4*300 mL).The organics were combined, dried and then evaporated in vacuo.The residue (ca. 4.0 g) was suspended in a mixture of MeOH (100 mL), THF (100 mL) and water (100 mL) and treated with NaBH4 (1.57 g, 41.4 mmol).After stirring for 1 hr a solution of NaOH (1M, 20 mL) was added and the mixture was allowed to stand at RT for 48 hr.The solvents were evaporated to give a yellow solid which was partitioned between water (50 mL) and EtOAc (100 mL).The solid which formed at the interface was removed by filtration and the aq layer was extracted with THF (3*300 mL) then dried and evaporated to give a yellow solid.The material was suspended in THF (100 mL) and MeOH (50 mL) and absorbed onto silica gel (20 g) and subjected to column chromatography (80 g, 15percent MeOH in DCM isocratic elution) to give (2-aminopyrimidin-4-yl)methanol (69) as an off-white solid (720 mg, 7percent): m/z 126 (M+H)+ (ES+).

Statistics shows that 165807-05-6 is playing an increasingly important role. we look forward to future research findings about 4-Dimethoxymethylpyrimidin-2-ylamine.

Reference:
Patent; Charron, Catherine Elisabeth; Fenton, Robert; Crowe, Scott; Ito, Kazuhiro; Strong, Peter; Rapeport, William Garth; Ray, Keith; US2012/244120; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5177-27-5 ,Some common heterocyclic compound, 5177-27-5, molecular formula is C4H3Cl2N3, 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.

3.2 g of 5-amino-2,4-dichloropyrimidine in 50 ml ethyl acetate were added to a mixture of 25 ml of saturated aqueous sodium bicarbonate solution and 25 ml of water. At room temperature, a solution of 4.9 g of 3,5-dimethyl-4-methoxybenzoyl chloride was added over a period of 15 min. The mixture was stirred intensively for 4 h. The layers were then separated, after which the aqueous layer was extracted twice with ethyl acetate. After drying over sodium sulfate and filtration, the solvent was removed under reduced pressure, giving 7.54 g of crude product. The crude product was triturated with 25 ml of isopropanol. Filtration and washing with 10 ml of isopropanol gave 2.74 g of the title compound in the form of a white solid. LC/MS (Method LC2): Rt=1.00 min; m/z=326.0; 328.0 [M+H]+ (dichloro pattern)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5177-27-5, its application will become more common.

Reference:
Patent; SANOFI; KADEREIT, Dieter; SCHAEFER, Matthias; HACHTEL, Stephanie; HUEBSCHLE, Thomas; HISS, Katrin; HAAG-DIERGARTEN, Silke; US2013/23545; (2013); 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.51-20-7, name is 5-Bromouracil, molecular formula is C4H3BrN2O2, molecular weight is 190.9828, as common compound, the synthetic route is as follows.name: 5-Bromouracil

General procedure: To a suspension of appropriate pyrimidine base (2 equiv.) in toluene were added triethylamine (4.1 equiv.) and trimethylsilyl trifluoromethanesulfonate (6.1equiv.) and the mixture were stirred at room temperature for 1h. The silylated base solution was diluted with additional dichloromethane and this solution was then added to a solution of 10 in dichloromethane dropwise over a period of 20 min at 0C. An additional amount of triethylamine (2.1equiv.) was added dropwise to the reaction mixture to initiate the Pummerer reaction at 0C. After the reaction mixture was stirred at room temperature for 15h, the reaction mixture was quenched with saturated NaHCO3 and extracted with dichloromethane. The organic layers were washed with saturated NaHCO3 solution, water and brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified on flash silica gel column chromatography (hexane:ethyl acetate=2:1) to give the beta-anomers 11a-11f.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51-20-7, 5-Bromouracil, and friends who are interested can also refer to it.

Reference:
Article; Kim, Jin-Hee; Yu, Jinha; Alexander, Varughese; Choi, Jung Hee; Song, Jayoung; Lee, Hyuk Woo; Kim, Hea Ok; Choi, Jungwon; Lee, Sang Kook; Jeong, Lak Shin; European Journal of Medicinal Chemistry; vol. 83; (2014); p. 208 – 225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 89283-48-7, 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 89283-48-7, name is 4-Chloro-6-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of NaH (1.98 g, 50 mmol, 60% in oil) in DMSO (20 mL) is added dimethyl malonate (5.67 mL, 50 mmol) at 23C (cooled by ice-water if necessary). After the evolution of hydrogen has ceased, 4-chloro-6-methylsulfanyl-pyrimidine 2 (3.22 g, 20 mmol) is added. The reaction is further heated at 8O0C for 5 hours. The reaction mixture is then cooled to room temperature, and quenched with saturated NH4Cl solution (50 mL). The organics are extracted with ethyl acetate (3 x 60 mL). The combined organic layers are washed with brine (2x) and dried over Na2SO4, filtered and concentrated. 50 mL of hexanes are added to the residue and heated at 600C for half hour and then cooled to room temperature. The solid is filtered and washed with hexanes to afford 2-(6-methylsulfanyl- pyrimidin-4-yl)-malonic acid dimethyl ester. (If necessary, the hexanes washing can be concentrated and purified by silica gel flash chromatography eluting with ethyl acetate in hexanes from 0% to 40% to afford additional product). 1H NMR 400 MHz (DMSO-d6) Compound A delta 8.92 (s, IH), 7.53 (s, IH), 5.20 (s, I H) 3.70 (s, 6H), 2.56 (s, 3H); Compound B (tautomer of A, the structure is tentatively assigned) 8.37 (s, IH), 7.34 (s, IH), 3.66 (s, 6H), 2.48 (s, 3H).

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 89283-48-7, 4-Chloro-6-(methylthio)pyrimidine.

Reference:
Patent; IRM LLC; WO2008/8747; (2008); 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. 3438-48-0, name is 4-Phenylpyrimidine, molecular formula is C10H8N2, 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. Recommanded Product: 4-Phenylpyrimidine

(Step 1: Synthesis of di-mu-chloro-bis[bis(4-phenylpyrimidine)iridium(III)] (abbreviation: [Ir(ppm)2Cl]2))First, into a three-neck flask equipped with a reflux pipe were put 30 mL of 2-ethoxyethanol, 10 mL of water, 0.67 g of a ligand 4-phenylpyrimidine (abbreviation: Hppm), 0.50 g of iridium chloride (IrCl3-HCl H20), and the air in the three-neck flask was replaced with nitrogen. After that, the mixture was heated and refluxed for 13 hours to be reacted. The reacted solution was cooled naturally to room temperature and filtered. The substance obtained by the filtration was washed with ethanol to give a dinuclear complex [Ir(ppm)2Cl]2 (red powder, yield of 42 %). A synthesis scheme (d-1) of Step 1 is shown below.

With the rapid development of chemical substances, we look forward to future research findings about 3438-48-0.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; INOUE, Hideko; YAMAGUCHI, Tomoya; SHITAGAKI, Satoko; USHIKUBO, Takahiro; SEO, Satoshi; YAMADA, Yui; NOWATARI, Hiromi; WO2012/53627; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia