Pyrimidines

Synthetic Route of 25940-35-6 , The common heterocyclic compound, 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C7H5N3O2, 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.

Thionyl chloride (8.92 mL, 123 mmol) was added to pyrazolo[l,5-a]pyrimidine- 3-carboxylic acid (0.2 g, 1.2 mmol) and the mixture was stirred for 2 h at 80 C. The solvent was then removed under reduced pressure and the material was left on the high-vacuum for 3 h. The material was used without further purification.

The synthetic route of 25940-35-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; CHILDERS, Matthew, L.; GIBEAU, Craig, R.; HO, Ginny Dai; TSUI, Honchung; (80 pag.)WO2016/144844; (2016); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90213-67-5, 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, 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 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, blongs to pyrimidines compound. Quality Control of 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

A suspension of 2, 4-dichloro-7-methyl-7H-pyrrolo [2, 3-d] pyrimidine (200 mg, 0.99 mmol) , (+/-) -trans-methyl 3-aminobicyclo [2.2.2] octane-2-carboxylate (200 mg, 1.09 mmol) and K2CO3(273 mg, 1.98 mmol) in DMF (10 mL) was stirred at rt overnight. The reaction was quenched with H2O (100 mL) , and the resulting mixture was extracted with ethyl acetate (50 mL × 3) . The combined organic layers were washed with saturated brine (100 mL) , dried over anydrous Na2SO4,filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 3/1) to give the tilte compound as a white solid (144 mg, 42 %) .MS (ESI, pos. ion) m/z: 349.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90213-67-5, 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (0 pag.)WO2018/157830; (2018); A1;,
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Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 14080-23-0, name is 2-Cyanopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 14080-23-0

l-(pyrimidin-2-yl)ethenone may be prepared as follows:A solution of pyrimidine-2-carbonitrile (75 g, 713.62 mmol) in THF (750 ml, 10 vol) was added dropwise to a solution of Methylmagnesium bromide (3.0M in diethylether) (357 ml, 1070.44 mmol) in THF (750 ml) at -5C. The resulting yellow suspension/solution was stirred at O0C overnight, and added to a rapidly stirred mixture of saturated ammonium chloride solution (750 ml) and 4M HCl (450 ml) at 5C, then pH adjusted to 1 with additional 2M HCl (5mL). The solution was warmed to 2O0C, stirred for 40 minutes, cooled to 00C then pH adjusted to 6.5-7 by addition of saturated K2CO3 solution (37.5 ml), warmed to 1O0C and separated. The aqueous phase was further extracted into ethyl acetate (5 x 750 ml). Sodium chloride was added to saturate the aqueous phase, which was extracted further into ethyl acetate (750 ml). The pH of the aqueous phase was adjusted to 7-8 by addition of saturated K2CO3 solution, and extracted further with ethyl acetate (3 x 750 ml). The combined organics were washed with saturated brine (750 ml), dried over MgSO4, filtered and concentrated in vacuo to give 78.9g of a brown solid. The crude product was purified by flash silica chromatography, elution in EtOAc. Pure fractions were evaporated to dryness to afford 1- (pyrimidin-2-yl)ethanone (65.Og, 74.6 %) as a yellow crystalline solid. 1H NMR (400.132 MHz, DMSO) delta 2.67 (3H, s), 7.72 (IH, t), 9.02 (2H, d); m/z (M+H)+, 123.

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, 14080-23-0, 2-Cyanopyrimidine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/117051; (2008); A1;,
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Pyrimidine – Wikipedia

Application of 1193-24-4, 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 1193-24-4 as follows.

A mixture of DMF (64 mL) and POCl3 (200 mL) at 0 C. was stirred for 1 h, treated with 4,6-pyrimidinediol (50.0 g, 446 mmol), and stirred for 0.5 h at rt, and then refluxed for 3 h. The volatiles were removed under reduced pressure, and the residue was poured into ice water and extracted six times with Et2O. The organic phase was washed with satd. aq. NaHCO3 and water, dried over Na2SO4, concentrated, and crystallized (EtOAc-petroleum ether) to give 4,6-dichloro-5-pyrimidinecarbaldehyde; LC-MS (ESI) m/z 177 [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,1193-24-4, its application will become more common.

Reference:
Patent; AMGEN INC.; US2011/245257; (2011); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 1005-37-4 , The common heterocyclic compound, 1005-37-4, name is 6-Chloro-N4-methylpyrimidine-2,4-diamine, molecular formula is C5H7ClN4, 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.

Intermediate 44 6-(4-aminophenyl)-4-N-methylpyrimidine-2,4-diamine. Tetrakis(triphenylphosphine)palladium (0) (5 mol%) was added to a stirred mixture of 6-chloro-4-N-methylpyrimidine-2,4-diamine (1.0 mmol), 4-(tetramethyl- 1 ,3,2-dioxaborolan-2-yl)aniline (1.3 equiv.), sodium carbonate (3.2 equiv.), 1 ,4- dioxane (4 ml_) and water (1 ml_) in a tube. The tube was sealed and the reaction was heated at 90C for 5 h and then concentrated. The crude material was taken up in ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate, concentrated and purified by flash chromatography (0?15 % MeOH/DCM) to give the title compound. LCMS [M+H]+ 216; 1 H NMR (400 MHz, CDCIs) delta ppm 7.64 (2 H, d, J=8.53 Hz), 6.50 – 6.62 (3 H, m), 6.03 (1 H, s), 5.74 (2 H, s), 5.37 (2 H, s), 2.76 (3 H, d, J=4.77 Hz).

The synthetic route of 1005-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); 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 5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 5751-20-2

2-Methylsulfanyl- 1 H-pyrimidin-6-one (4.81 g, 33.8 mmol), tert-butyl 4- [[4- [(iS)1-aminoethyllphenyllmethyllpiperazine-1-carboxylate (9.00 g, 28.2 mmol), and DME (56 mL) are split equally into three microwave vessels that are sealed and heated to 120 °C for 4 days. The reaction mixtures are allowed to cool to room temperature, combined, concentrated, and resuspended in CH2C12. The solids are filtered away and the filtrate is adsorbed onto silica gel and chromatographed on silica gel eluting with a gradient of 1- 7percent MeOH/CH2C12 to give the title compound as an off-white solid (10.55 g, 22.45 mmol,88percent purity). ES/MS (mlz): 414 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 5751-20-2.

Reference:
Patent; ELI LILLY AND COMPANY; LUMERAS AMADOR, Wenceslao; BAUER, Renato A.; BOULET, Serge Louis; BURKHOLDER, Timothy Paul; GILMOUR, Raymond; HAHN, Patric James; CARBALLARES MARTIN, Santiago; RANKOVIC, Zoran; (80 pag.)WO2017/213910; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 26830-94-4 , The common heterocyclic compound, 26830-94-4, name is 2,6-Dichloropyrimidine-4-carbonyl chloride, molecular formula is C5HCl3N2O, 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.

Step 3: 6-(2,6-dichloro-pyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one 2.75 g (13.0 mmol) 2,6-dichloro-pyrimidine-4-carboxylic acid chloride, 1.94 g (13.0 mmol) 4-methyl-3H-benzoxazol-2-one and 6.93 g (52.0 mmol) aluminium trichloride were heated to 125 C. for 1.5 h with stirring. The mixture combined with ice water and the product precipitated as a solid was suction filtered, washed with water and dried i. vac. Yield: 3.70 g (88% of theoretical) ESI-MS: m/z=322 (M-H)-

The synthetic route of 26830-94-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/59954; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 115581-36-7, Adding some certain compound to certain chemical reactions, such as: 115581-36-7, name is 2-Chloro-5-(methylthio)pyrimidine,molecular formula is C5H5ClN2S, 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 115581-36-7.

EXAMPLE 4 N-[4-(1,3-benzodioxol-5-yl)-3-(2-{[5-(methylsulfanyl)-2-pyrimidinyl]oxy}ethoxy)-5-isoxazolyl]-4-(tert-butyl)benzenesulfonamide To a solution of N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-5-isoxazolyl]-4-(tert-butyl)benzenesulfonamide (Preparation 6) (109 mg) in tetrahydrofuran (3 mL), purged with nitrogen three times, was added sodium hydride (20 mg of a 60% dispersion in oil) and the reaction mixture stirred for 15 minutes. After which time a solution of 2-chloro-5-(methylsulfanyl)pyrimidine (42 mg) in dimethylformamide (0.5 mL) was added to the reaction mixture and then left stirring at room temperature overnight. The reaction mixture was quenched with citric acid (1.0M, 10 mL) and extracted into ethyl acetate (15 mL). The organics were washed with water (10 mL), brine (10 mL) and dried over magnesium sulfate before being concentrated in vacuo to yield the crude material (150 mg). This was purified by HPLC on a 5mu ODS Phenomenex Magellen column with a gradient elution of 0.1 M NH4OAc (95% to 50%) and acetonitrile (5% to 50%) to yield the desired product as a white solid (16 mg). deltaH (300 MHz, CDCl3): 8.50(2H, s), 7.80(2H, d), 7.60(1H, br), 7.50(2H, d), 6.80(2H, d), 6.65(1H, d), 5.95(2H, s), 4.70(2H, m), 4.60(2H, m), 2.45(3H, s), 1.35(9H, s) m/z (thermospray) [MH+]=584.7, C27H29N4O7S2 requires 584.7.

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. 115581-36-7, 2-Chloro-5-(methylthio)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Banks, Bernard Joseph; Chubb, Nathan Anthony Logan; Eshelby, James John; Pacey, Michael Stephen; Schulz, Darren John; US2002/19408; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3740-92-9, 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. 3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine, molecular formula is C10H6Cl2N2, 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.

In 250mL three-necked flask, purged with nitrogen, was added 0.01mol intermediate A20, 150mlDMF, 0.012mol intermediate B1, 0.0001mol palladium acetate, stirred,Then 0.01mol K3PO4 aqueous solution was added, heated to 150 , the reaction was refluxed for 24 hours, the sample point plate, the reaction was complete.The mixture was naturally cooled and extracted with 200 ml of dichloromethane. The layers were separated and the extract was dried over anhydrous sodium sulfate and filtered. The filtrate was rotary evaporated and purified over silica gel to give intermediate C1. HPLC purity was 99.2percent with a yield of 85.1percent.

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 3740-92-9, 4,6-Dichloro-2-phenylpyrimidine.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Zhang Zhaochao; Li Chong; (51 pag.)CN107417668; (2017); A;,
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. 5948-71-0, name is Ethyl 4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate, the common compound, a new synthetic route is introduced below. COA of Formula: C14H15ClN2O3

General procedure: To a solution of 3,4-dihydropyrimidin-2(1H)-one (1 mmol) in acetonitrile and water (10:2mL) in a 50 mL round-bottomed ask equipped with a condenser and a magnetic stirrer, 1,4-bis(triphenylphosphonium)-2-butene peroxo disulfate (1 mmol) was added in small portions.The reaction mixture was refluxed for the appropriate time indicated in Table 1. The progress of the reaction was monitored by TLC. Upon completion of the reaction, it was cooled to room temperature and filtered. Water (15 mL) was added and extracted with chloroform (3 × 15 mL). The combined organic layers solution was dried over MgSO4. The solvent was concentrated in vacuo; the resulting product was directly charged on a small silica gel column and eluted with a mixture of diethyl ether and n-hexane (1:4) to afford the pure product.

The synthetic route of 5948-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gorjizadeh, Maryam; Bulletin of the Korean Chemical Society; vol. 34; 6; (2013); p. 1751 – 1754;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia