Day: June 18, 2021

Adding a certain compound to certain chemical reactions, such as: 100644-65-3, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

To the product of Step 1 (15.0 g, 88 mmol) in DMF (150 ml) add 60% NaH in mineral oil (4.25 g, 106 mmol). Add slowly 1-bromo-2-chloroethane (22.1 ml, 265 mmol). Stir at RT 2 h, concentrate, and chromatograph on silica to obtain the dichloride as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100644-65-3, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US2005/239795; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 15783-48-9, 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. 15783-48-9, name is 2,4-Dichlorofuro[3,4-d]pyrimidin-7(5H)-one, molecular formula is C6H2Cl2N2O2, 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.

Step 3-Synthesis of (S)-2-chloro-4-(3-methylmorpholino)furo[3,4-d]pyrimidin-7(5H)-one (fr). A solution of (fq) (250 mg, 1.2 mmol) in dichloromethane (3 mL) was cooled in ice-bath. (S)-3-methylmorpholine (0.14 g, 1.3 mmol) was added followed by DIPEA (0.23 mL, 1.3 mmol). The resulting dark red solution was stirred at rt for 2 h. It was diluted with 1 N HCl, and the phases separated. The aqueous layer was extracted with dichloromethane (2×). The combined dichloromethane extract was dried over MgSO4, filtered, concentrated in vacuo to give 280 mg (85%) of (fr) as a yellow solid; LC-MS: m/z=+270 (M+H)+.

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 15783-48-9, 2,4-Dichlorofuro[3,4-d]pyrimidin-7(5H)-one.

Reference:
Patent; Genentech, Inc.; US2010/331305; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4270-27-3, 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. 4270-27-3, name is 6-Chloropyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

General procedure: 6-Chloropyrimidine-2,4(1H, 3H)-dione derivatives 1 (1.0 mmol) and N-hydroxyformimidoyl chloride derivatives 2 (1.2 mmol) were combined and dissolved in methanol (15mL), followed by the addition of triethylamine (3.0 mmol). Subsequently, the reaction mixture was stirred in a round-bottom flask (25mL) at room temperature for 5h. After completion of the reaction as indicated by TLC, the mixture was evaporated by rotary evaporator, extracted with ethyl acetate, dried over Na2SO4, then concentrated and purified by flash column chromatography (PE/EA=5:1) to yield compounds 3a-t.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4270-27-3, 6-Chloropyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Kun-Ming; Jin, Yi; Lin, Jun; Tetrahedron; vol. 73; 47; (2017); p. 6662 – 6668;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 57489-77-7, 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.57489-77-7, name is 5,7-Dichloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H3Cl2N3, molecular weight is 188.01, as common compound, the synthetic route is as follows.

Example 3; [A General Procedure for the Synthesis of a Pyrazolo[1,5-a]pyrimidine Derivative Represented by General Formula (V-04)]; A mixture was prepared by adding N-chlorosuccinamide, N-bromosuccinamide or iodine monochloride (0.011 mol) to a chloroform (50 mL) solution containing 5,7-dichloropyrazolo[1,5-a]pyrimidine (V-03) (0.01 mol) at room temperature. The mixture was stirred under heating and reflux until all solid was dissolved and the starting materials disappeared by TLC. The mixture was poured into ice/water to separate the organic layer, which was washed with aqueous Na2CO3 solution, subsequently dried with MgSO4, and the solvent was removed under vacuum. The residue was purified by silica gel chromatography to obtain 3-halo-5,7-dichloropyrazolol,5-alpyrimidine (V-04). The typical yield of the reaction ranged from 60 to 90%.

Statistics shows that 57489-77-7 is playing an increasingly important role. we look forward to future research findings about 5,7-Dichloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; TEIJIN PHARMA LIMITED; US2006/135514; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 57054-92-9, 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. 57054-92-9, name is 5-Bromo-2-chloro-4-methoxypyrimidine, molecular formula is C5H4BrClN2O, 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.

Nitrogen was bubbled for 5 minutes through a mixture of 5-bromo-2-chloro-4- methoxypyrimidine (Preparation 25a, 0.51 g, 2.3 mmol), pyridin-3-yl boronic acid (0.30 g, 2.5 mmol) and potassium carbonate (0.93 g, 6.7 mmol) in toluene (8.0 mL) and Nu,Nu’- dimethylformamide (1.0 mL) contained in a microwave vessel. Then [1 , 1 – bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (1 :1) (68 mg, 0.1 1 mmol) was added and the vessel was sealed and subjected to microwave irradiation for 10 minutes at 185 C. The reaction mixture was filtered through Celite, washing the filter cake with ethyl acetate. The combined filtrate and washings were evaporated and the residue was purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (0.066 g, 1 %) as a solid.LRMS (m/z): 222 (M+1)+

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 57054-92-9, 5-Bromo-2-chloro-4-methoxypyrimidine.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; BACH TANA, Jordi; PAGES SANTACANA, Lluis Miquel; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; MATASSA, Victor Giulio; WO2011/76419; (2011); 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.1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, molecular weight is 134.14, as common compound, the synthetic route is as follows.COA of Formula: C6H6N4

General procedure: Procedure G: To a solution of 7H-pyrrolo[2,3-d]pyrimidin-4-amine (1, 0.32 g, 2.39 mmol) and 2?-chloro-4?-methylspiro[cyclohexane-1,7?-pyrrolo[3,4-b]pyridin]-5?(6?H)-one (2, 0.6 g, 2.39 mmol) in 1,4-dioxane (15 mL) was added cesium carbonate (2.33 g, 7.17 mmol). The reaction mixture was purged with argon for 5 min. and then XanthPhos (69 mg, 0.11 mmol), XPhos (57 mg, 0.11 mmol), tris(dibenzylideneacetone)dipalladium(0) (109 mg, 0.11 mmol) and palladium acetate (27 mg, 0.11 mmol) were added and the reaction mixture purged for an additional 5 min. The purged reaction mixture was stirred at 100 C. for 4 h. After TLC showed completion, the reaction mixture was filtered through a bed of celite and the resulting filtrate was concentrated. The crude product was purified by preparative HPLC. The desired fractions were concentrated to dryness under vacuum to afford 2?-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4?-methylspiro[cyclohexane-1,7?-pyrrolo[3,4-b]pyridin]-5?(6?H)-one as a yellow solid. Yield: 0.095 g, 11%;

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); 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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide, molecular formula is C5H4ClN3O, 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. Safety of 2-Chloropyrimidine-4-carboxamide

Similar to as described in General Procedure X, 2-chloropyrimidine-4-carboxamide was reactedwith (3-bromo-2-fluorophenyl)boronic acid to afford the title compound (450 mg, 48%) as ayellow solid. LC-MS (ES, m/z): 296 [M+H]. Aryl halide, palladium (II) bis(triphenylphosphine) dichloride or tetrakis (triphenylphosphine) palladium (0.OSeq), boronic acid or pinacol ester (1. leq) and cesium fluoride (2eq) were weighed out into a microwave vessel or sealed tube. Ethanol (3 mL/mmol) and water (0.6 mL/mmol) were added. The vessel was capped and heated thermally or in a microwave vessel at 70-400 C for 1 hour. The reaction mixture was concentrated under vacuum and the residue was purified by silicagel column chromatography to afford the Suzuki coupling product.

With the rapid development of chemical substances, we look forward to future research findings about 22536-66-9.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
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. 7234-25-5, name is Ethyl 4-Methyl-2-(methylthio)-5-pyrimidinecarboxylate, the common compound, a new synthetic route is introduced below. Recommanded Product: 7234-25-5

b. Preparation of 4-((E)-2-Dimethylamino-vinyl)-2-methylsulfanyl-pyrimidine-5- carboxylic acid ethyl ester 5.4-Methyl-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester 3 (18.0 g, 84.8 mmol) was dissolved in DMF (5OmL), N.N-Dimethylformamiddimethylacetal (22.5 ml_, 170 mmol) and stirred at reflux for 3 hours. Then mixture was concentrated, the residue was dissolved in TCM, washed with water, dried, filtered, and concentrated. The prod- uct was purified by crystallization from ether to yield in a colorless solid (14.0 g, 52.5 mmol, 62 %).

The synthetic route of 7234-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; SCHIEMANN, Kai; SCHULTZ, Melanie; STAEHLE, Wolfgang; KOBER, Ingo; WIENKE, Dirk; KRIER, Mireille; WO2010/63352; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3764-01-0, 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 3764-01-0, name is 2,4,6-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1 : Synthesis of 2-[2-(pyridin-2-yl)-ethoxy]-4-[N’-(3-methyl-benzilidene)- hydrazino]-6-(morpholin-4-yl)-pyrimidine (Compound 6) EPO Step 1.A 2-liter, 3-neck flask equipped with mechanical stirrer, thermometer and dropping funnel was loaded with ethanol (375 mL), water (375 mL) and morpholine, (1.01 mol, 88 g); the resulting solution was cooled (with sodium chloride- ice mixture) to about 0 0C and a solution of 2,4,6-trichloropyrimidine (91.17 g, 0.5 mol) in ethyl acetate (37.5 mL) was added dropwise in about 20 minutes, to maintain temperature below 10 0C. The dropping funnel was rinsed twice with ethyl acetate (3 mL), and the rinses were transferred to the reaction mixture. The reaction was checked by TLC to determine when the reaction was complete. After completion of the reaction, ice water (375 mL) was added, and reaction was allowed to stir for 30 minutes to complete precipitation. The colorless solid was filtered out, washed 6 times with water (225 mL per wash) and vacuum-dried at 40-50 0C until a constant weight of the product was maintained. The product (114.7 g, 98% yield) was a mixture of regioisomers 2,4-dichloro-6-(morpholin-4-yl)-pyrimidine and 4,6-dichloro-2- (morpholin-4-yl)-pyrimidine in about a 3.9: 1 ratio (Product 1).

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/53112; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 582313-57-3, Adding some certain compound to certain chemical reactions, such as: 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H3ClFN3, 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 582313-57-3.

To containCCl4 (5 mL, 51 mmol)Add hexamethylphosphoramide to a solution of 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose (9.13 g, 30 mmol) in toluene (100 mL) 7.2 mL, 40 mmol). After stirring at 0 C for 2.5 hours,The reaction mixture was added to 4-chloro-5-fluoro-7H-pyrrole [2,3-d]pyrimidine (14-1, 3.1 g,20 mmol), a solution of tris(3,6-dioxaheptyl)amine (TDA-1) (3 mL, 9 mmol) and KOH (2.6 g, 4.5 mmol) in toluene (100 mL)The entire reaction mixture was stirred at room temperature for 24 hours.The reaction was terminated by the addition of a saturated aqueous solution of NH 4 Cl.Transfer the entire mixture to a separatory funnel. The aqueous layer is extracted with AcOEt.The combined organic layers were washed with brine.Dry (Na2SO4)Concentration in vacuo gave the crude product 17-2.

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. 582313-57-3, 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Hongyi Biological Technology Co., Ltd.; Wu Rongguang; Yi Dewu; (140 pag.)CN109694397; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia