Pyrimidines

Synthetic Route of 75833-38-4, 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 75833-38-4, name is 2-Chloropyrimidine-4-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-chloropyrirnidine-4-carbonitrile (900 mg, 6.45 mmol) in dioxane (8 mL)/water (2 mL) was added K2C03 (2.20 g, 16.12 mmol), Pd(dppf)Cl2 (1.0 g, 1.29 mmol) and 4,4,5, 5-tetramethyl-2-vinyl-l,3,2-dioxaborolane (1.5 g, 9.67 mmol). The resulting mixture was stirred at 90 C overnight. After cooling to RT, the mixture was diluted with water (10 mL) and extracted with EtOAc (30 mL x 3). The combined organic layers were washed with brine, dried over Na2SC>4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography column (9% EtOAc in petroleum ether) to give the title compound as a solid. LRMS m/z (Mu+Eta) 132.1 found, 132.1 required.

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 75833-38-4, 2-Chloropyrimidine-4-carbonitrile.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel; LUO, Yunfu; (85 pag.)WO2016/100156; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1208901-69-2, Adding some certain compound to certain chemical reactions, such as: 1208901-69-2, name is 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride,molecular formula is C7H8Cl3N3, 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 1208901-69-2.

2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride (20.0 g, 83.2 mmol) prepared according to Reference Example 1 was dissolved in acetonitrile (200 mL), and the solution was mixed with dimethylaminopyridine (752 mg), di-tert-butyl dicarbonate (20.9 g) and triethylamine (11.6 mL), followed by stirring at room temperature for sixteen hours. After checking the completion of the reaction by thin layer chromatography, the reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The solution was sequentially washed with a 5% aqueous citric acid solution, water, a saturated aqueous sodium bicarbonate solution and brine, was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) and thereby yielded tert-butyl 2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-6-car boxylate (22.2 g, in a yield of 88%).

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. 1208901-69-2, 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1552842; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1233026-31-7, 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 1233026-31-7 as follows.

Step 2: Potassium carbonate (0.89 g, 6.45 mmol) was added at room temperature to an oven-dried, nitrogen cooled flask containing a suspension of ethylene glycol (1.3 mL, 23.4 mmol) in DMF (29 mL) and the mixture was then stirred for 15 minutes. 2-Chloro-4- (methylsulfonyl)pyrimidine (1.13 g, 5.86 mmol) was then added. The solution was stirred for 1.5 h at room temperature, then diluted with EtOAc (30 mL) and washed with 1 : 1 watenbrine (3 x 50 mL). The organic extracts were dried over sodium sulfate, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes) to afford 2-[(2-chloropyrimidin-4-yl)oxy]ethanol as a pale yellow solid. MS ESI calcd. for C6H8C1 202 [M + H]+ 175, found 175.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1233026-31-7, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michele, R.; ALTMAN, Michael, D.; ROMEO, Eric, T.; VITHARANA, Dilrukshi; CASH, Brandon; SIU, Tony; ZHOU, Hua; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; HAIDLE, Andrew, M.; CHILDERS, Kaleen Konrad; MADDESS, Matthew, L.; REUTERSHAN, Michael, H.; DUCHARME, Yves; GUERIN, David. J.; SPENCER, Kerrie; BEAULIEU, Christian; TRUONG, Vouy Linh; GUAY, Daniel; NORTHRUP, Alan, B.; TAOKA, Brandon, M.; LIM, Jongwon; FISCHER, Christian; BUTCHER, John, W.; OTTE, Ryan, D.; SUN, Binyuan; WO2013/192125; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 38696-21-8, 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. 38696-21-8, name is 5-Bromo-N,N-dimethylpyrimidin-2-amine, molecular formula is C6H8BrN3, 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.

A mixture of 5-bromo-N,N-dimethylpyrimidin-2-amine (0.966 g, 4.78 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.46 g, 5.74 mmol), PdCl2dppf(DCM) (0.114 g, 0.14 mmol) and KOAc (1.407 g, 14.34 mmol) were placed under Ar in a 20 mL microwave flask. Anhydrous 1,2-dimethoxyethane (16 mL) was added and the flask was irradiated at 150 oC for 15 minutes. The reaction was filtered through celite, concentrated and slurried in EtOAc. The reaction was filtered through celite again and the organics were concentrated and purified by column chromatography 0 to 30 % EtOAC in Hexanes. The material was isolated as a light teal solid (0.718 g, 60 % yield). 1H NMR (400 MHz, CDCl3) delta 8.59 (s, 2H), 3.21 (s, 6H), 1.31 (s, 12H).13C NMR (100 MHz, CDCl3) delta 164.1, 83.7, 77.4, 37.2, 25.2, 24.9. HRMS (EI+) m/z calculated for C12H12BN3O2 [M+H]+: 250.1721, found: 250.17189.

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 38696-21-8, 5-Bromo-N,N-dimethylpyrimidin-2-amine.

Reference:
Patent; EMORY UNIVERSITY; SHI, Qi; KAISER, Thomas; DIRADDO, John; SNYDER, James P.; LIOTTA, Dennis C.; DENTMON, Zackery; (67 pag.)WO2017/197151; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 126352-69-0, 4,5,6,7-Tetrahydropyrazolo[1,5-a]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, Application In Synthesis of 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine

N-Iodosuccinimide (0.581 g, 2.58 mmol) was added to 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (0.265 g, 2.15 mmol) in acetonitrile (5 mL) at r.t. under nitrogen. The resulting solution was stirred at r.t. for 1 h before water (20 mL) was added. Stirring was continued for 1.5 h, and then the reaction mixture was extracted with MTBE (3×20 mL). The combined organic layers were washed sequentially with 2 M aqueous NaOH (20 mL), Na2S2O3 solution (20 mL, 10% w/v), and saturated aqueous sodium chloride (20 mL) before being dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford 3-iodo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (0.155 g, 28.9%) as a white crystalline solid. 1H NMR (400 MHz, CDCl3, 30 C.) 2.16 (2H, q), 3.32-3.44 (2H, m), 3.98 (1H, s), 4.12 (2H, t), 7.24 (1H, s). m/z: ES+[M+H]+ 250.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,126352-69-0, 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; Barlaam, Bernard; De Savi, Christopher; Hawkins, Janet; Hird, Alexander; Lamb, Michelle; Pike, Kurt; Vasbinder, Melissa; (134 pag.)US2016/376287; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7355-55-7, 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 7355-55-7, name is 2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one. This compound has unique chemical properties. The synthetic route is as follows.

2-Amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (1.5 g, 0.01 mol) at room temperatureIodine (5.1 g, 0.02 mol) was dissolved in ethanol/water (2:1, 100 mL) and heated to reflux for 2 h.The precipitate was cooled and precipitated, and the precipitate was filtered, washed with 1N sodium thiosulfate solution (2×30 mL) and water (2×50 mL).After drying, 2-amino-6-iodo-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one was obtained.

According to the analysis of related databases, 7355-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hebei Medical University; Wang Lei; Liu Yi; Zhang Congying; Gao Tianfeng; Zheng Qianqian; (37 pag.)CN110078735; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-65-8, Adding some certain compound to certain chemical reactions, such as: 22536-65-8, name is 2-Chloro-5-methoxypyrimidine,molecular formula is C5H5ClN2O, 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 22536-65-8.

A MW reaction vessel was charged with 2-chloro-5- methoxypyrimidine (0.817 g, 5.65 mmol) and 25% NH3(aq). The vessel was capped and heated to 150 0C for 3h. The mixture was evaporated to dryness. The resulting material was dissolved in CH2Cl2MeOH (1 : 1) and adsorbed onto silica. Purification by flash CC (eluent: 50-100 % EtOAc in heptane) gave the title compound as colorless crystals (386 mg, 55%). 1H NMR (400 MHz, dmso-d6) delta 8.02 (s, IH), 6.06 (br s, IH), 3.71 (s, 3H).

According to the analysis of related databases, 22536-65-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; WO2008/141239; (2008); A1;,
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. 69696-35-1, name is 5-Bromo-4-chloro-2,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below., COA of Formula: C6H6BrClN2

c) 5-bromo-2,4-dimethylpyrimidine. A mixture of 5-bromo-4-chloro-2,6- dimethylpyrimidine (2.73 g, 12.33 mmol), 4-methylbenzenesulfonohydrazide (4.19 mL, 37.0 mmol) and chloroform (40 mL) was heated at 90 C for 16 hours. The solution was cooled and the solid filtered and washed with chloroform. LCMS revealed this solid (4.75g) was the desired intermediate. A mixture of this solid and 0.94M aqueous sodium carbonate (40 mL, 37.7 mmol) was heated at 90 C for 1 .5 hours. The cooled solution was extracted with ethyl acetate 3 times, and the combined organics were washed with brine, dried (Na2S04) and concentrated to afford the title compound (1 .17 g, 51 %) as a tan oil, which crystallized upon standing. LCMS (ES+) m/e 187 [M+H]+.

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, 69696-35-1, 5-Bromo-4-chloro-2,6-dimethylpyrimidine.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROWN, Kristin, K.; CHAI, Deping; DODSON, Christopher, S.; DUFFY, Kevin, J.; SHAW, Antony, Nicholas; WO2013/96151; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4316-98-7 ,Some common heterocyclic compound, 4316-98-7, molecular formula is C4H5ClN4, 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.

A mixture of 4-(1-(2,2-difluoroethyl)piperidin-4-yl)benzoic acid (837 mg), 6- chloro-4,5-diaminopyrimidine (494 mg) in POCI3 (10 ml.) was heated at 120 C for 16 hrs. After it was cooled to room temperature, the residue was washed several times with ether. Then the residue was dissolved in small amount of MeOH, purified by silica gel column using 5-25% of MeOH in CH2CI2 as eluent to give 6-chloro-8-(4-(1-(2,2- difluoroethyl)piperidin-4-yl)phenyl)-9H-purine. LCMS-ESI+ (m/z): [M+H]+ calcd for C 8H1 8 CIF2N5: 378.1 ; found: 378.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4316-98-7, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; DU, Zhimin; GUERRERO, Juan, Arnaldo; KAPLAN, Joshua, Aaron; KNOX, JR., John Edward; NADUTHAMBI, Devan; PHILLIPS, Barton, W.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William, J.; ZABLOCKI, Jeff; WO2015/187684; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1780-27-4, 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.1780-27-4, name is 4,5,6-Trichloropyrimidine, molecular formula is C4HCl3N2, molecular weight is 183.42, as common compound, the synthetic route is as follows.

0.56 g of sodium hydride (60% oil suspention) was suspended in 18 ML of tetrahydrofuran. 2 ml of tetrahydrofuran solution of 0.8 g of 2-BUTYN-1-OL was added dropwise at room temperature therein slowly, and the mixture was stirred for 20 minutes. Into the mixture was added dropwise 5 ml of tetrahydrofuran solution of 3 g of 4,5, 6-TRICHLOROPYRIMIDINE at 0C slowly, and stirred for 2 hours. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with ethyl acetate three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 2.23 g of 4, 5-DICHLORO-6- (2-BUTYNYLOXY) pyrimidine. LH-NMR : 1.88 (t, 3H), 5.08 (q, 2H), 8.48 (s, 1H)

Statistics shows that 1780-27-4 is playing an increasingly important role. we look forward to future research findings about 4,5,6-Trichloropyrimidine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2004/99160; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia