Tag: M.W:200-300

Reference of 63558-65-6 ,Some common heterocyclic compound, 63558-65-6, molecular formula is C4H2ClIN2, 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: tert-Butyl (lR)-7-chloro-l-(5-formyl-2-methyi-3-thienyl)-3,4-dihydro-lH-isoquinoline- 2-carboxylate [00994] A solution of 4-chloro-5-iodopyrimidine (27.85 g, 1 16 mmol) in THF (280 mL) was cooled to -78 C with a dry-ice/MeOH bath. To the solution was added dropwise 2.50 M of n-BuLi in hexane (93 mL, 233 mmol) and the mixture was allowed to stir for 15 min at -78 C. To the mixture was added dropwise a solution of tert-butyl (lR)-7-chloro- l-(5-formyl-2-methyl-3- thienyl)-3,4-dihydro- lH-isoquinoline-2-carboxylate (27 g, 68.5 mmol) in THF (90 mL) at -75 C, and the resulting mixture was allowed to stir for 10 min at -40C followed by stirring for 30 min at 26 C. The reaction was quenched by addition of saturated aqueous NH4C1 (560 mL) and extracted with EtOAc (600 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo to provide 90 g of a maroon oil which was used without further purification. This step can also be done using a magnesium-halogen exchange (such as isopropylmagnesium chloride lithium chloride complex). Solvent for this transformation can alternatively comprise MeTHF. This reaction also can be run at 0 C to room temperature.The crude mixture was divided into three portions (30g, 59 mmol each) and each portion was dissolved in DCM (500 mL). Manganese (IV) oxide (86.7 g, 1 mol) was added to each solution and the reactions were allowed to stir at 30C for 4 h, at which point they were combined and filtered through a Celite pad. The filter cake was rinsed with DCM MeOH (100/1 , 500 mL x 3). The filtrate was concentrated in vacuo and the residue was purified by column chromatography eluting with 90/10 to 85/15 pentane/EtOAc gradient to provide 40 g (58% in 2 steps) of the title compound as a light yellow solid. The oxidation of tert-butyl ( l R)-7-chloro- l – (5-((4-chloropyrimidin-5-yl)(hydroxy)methyl)-2-methylthiophen-3-yl)-3,4-dihydroisoquinoline- 2(l H)-carboxylate can also be done using TEMPO/NaCIO reaction conditions. LCMS: (AA) M+Na 522.6.

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. 63558-65-6, 4-Chloro-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DUFFEY, Matthew O.; ENGLAND, Dylan; FREEZE, Scott; HU, Zhigen; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; ONO, Koji; XU, He; (684 pag.)WO2016/4136; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 18740-39-1, 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.18740-39-1, name is 2,4-Dichlorothieno[2,3-d]pyrimidine, molecular formula is C6H2Cl2N2S, molecular weight is 205.0645, as common compound, the synthetic route is as follows.

Weighing 4-hydroxy-3,5-dimethylbenzaldehyde (4.02 g, 26.7 mmol) and potassium carbonate (5.04 g, 36.6 mmol) in 150 mL of N,N-dimethylformamide (DMF), Stir at room temperature for 15 minutes.Then, 2,4-dichlorothieno[2,3-d]pyrimidine (5.0 g, 24.4 mmol) was added and the mixture was stirred at room temperature for 1 h (TLC detection reaction was completed).At this time, a large amount of white solid was formed, and 250 mL of ice water was slowly added thereto, filtered, and dried in a vacuum drying oven.It is then recrystallized from chloroform to give the compound 4-((2-chlorothieno[2,3-d]pyrimidin-4-yl)oxy)-3,5-dimethylbenzaldehyde 14 as a white solid.The yield was 92.7percent.

Statistics shows that 18740-39-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichlorothieno[2,3-d]pyrimidine.

Reference:
Patent; Shandong University; Liu Xinyong; Kang Dongwei; Zhan Peng; (25 pag.)CN108440559; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10244-24-3, 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. 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine. A new synthetic method of this compound is introduced below.

A reactor was charged with N-(5-bromo-4-(trifl uoromethyl)pyrid in-2-yl )acetamide (1 .405 m mol)and tetrahydrofuran (2 mL). The mixture was sitrred for 10 minutes. The mixture was cooled to0 C within 30 minutes. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (ml, 1.405mmol) was continuously added within a time period of 1 hour at 0 C. An additional 1.5 equivalents of isopropylmagnesiumcloride lithium chloride 1 .3M in THF (4.788 ml, 2.107 mmol) was continuously added within a time period of 1 .5 hours at 0 C. The product was the dianion of N-(5-bromo-4-(trifluoromethyl)pyridin-2-yl)acetamide, as determined by HPLC and LCMS.The compound 4,4?-(6-chloropyrimidine-2,4-diyl)dimorpholine (0.40g, 1.405 mmol), 1,1?- Bis(diphenylphosphino)ferrocene (0.040g, 0.070 mmol) and Palladium acetate (0.016g, 0.070 mmol) and 2 mL of tetrahydrofuran were placed in an inertized reactor. The reactor is evacuated to 100 mbar and flushed with nitrogen two times. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (1.405 mmol) was added at 30 C followed by an equivalent amount of the dianion of N-(5-bromo-4-(trifluoromethyl)pyridin-2-yl)acetamide (1.405 mmol) and 1- iodoadamantane (0.41 3g, 1 .405 mmol). The suspension was stirred for 0.5 hours. The product was N-(5-(2,6-dimorpholinopyrimidin-4-yl)-4-(trifluoromethyl)pyridin-2-yl)acetamide as determined by HPLC and LCMS.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10244-24-3, 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; FLUBACHER, Dietmar; BIERI, Nicole; ACEMOGLU, Murat; MICHEL, Pascal; MOSE, Rasmus; STETTLER, Hans; TESTA, Maria Caterina; BROZIO, Joerg; SCHAEFER, Frank; WO2014/64058; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10397-13-4, 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 10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of (S)-3-methylmorpholine (194 mg, 1.32 mmol, 1.5 eq.), i26 (300 mg, 1 .28 mmol, 1 .0 eq.) and A/,/V-diisopropylethylamine (3.0 eq.) in DMF (17 volumes) is heated for 16 hours (130 C). Then, the solvent is removed under reduced pressure. The residue is dissolved in dichloromethane (100 volumes) and washed with saturated aqueous sodium bisulfate (3 x 100 volumes). The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude mixture is purified by flash chromatography (Si02, cyclohexane/ethyl acetate 5:1 ) to afford the title compound i30 as a colorless solid (257 mg, 67%). 1H NMR (400 MHz, CDCI3): delta 5.84 (s, 1 H), 4.18 (m, 1 H), 3.94 (m, 2 H), 3.71 (m, 10 H), 3.53, (dt, 2JH,H = 12.0 Hz, 3JH,H = 3.1 Hz, 1 H), 3.20 (dt, 2JH,H = 12.8 Hz, 3JH,H = 3.8 Hz, 1 H), 1 .27 (d, 3JH,H = 6.8 Hz, 3 H); MS (MALDI): m/z = 298.4 ([M]+). -(4-chloro-6-morpholino-1 ,3,5-triazin-2-yl)morpholin-3-one (31 )

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 10397-13-4, 4-(4,6-Dichloropyrimidin-2-yl)morpholine.

Reference:
Patent; PIQUR THERAPEUTICS AG; UNIVERSITAeT BASEL; CMILJANOVIC, Vladimir; HEBEISEN, Paul; BEAUFILS, Florent; BOHNACKER, Thomas; RAGEOT, Denise; SELE, Alexander; WYMANN, Matthias; LANGLOIS, Jean-Baptiste; (217 pag.)WO2016/75130; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
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 1100318-96-4, name is 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

306) To a solution of 4-iodo-7H-pyrrolo[2,3-d]pyrimidine (2784.4 mg, 11.36 mmol) in dry THF (30.0 mL) was added pyridine (0,92 mL, 1 1.34 mmol), DIAD (4,7 mL, 23.82 mmol), tributylphosphane (5.7 mL, 22.68 mmol) and [(R)-(4-chlorophenyl)-[(2S,3S,4R)-3,4,5- trihydroxytetrahydrofuran -2-yl] methyl] 4-phenylbenzoate (Int-2-3) (5000.0 mg, 11.34 mmol) under N2. The reaction mixture was stirred at 30 C for 1 h under N2. LCMS showed the reaction was completed. The mixture was purified by silica chromatography column (DCM : CH OH = 100 : 1 to 60 : 1) to give [(R)-(4-chlorophenyl)-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(4-iodopyrrolo[2,3- d]pyrimidin-7-yl)tetrahydrofuran-2-yl]methyl] 4-phenylbenzoate (104a) (2.0 g, 2.99 mmol, 26.4% yield). LCMS [M+H] : 668.2.

With the rapid development of chemical substances, we look forward to future research findings about 1100318-96-4.

Reference:
Patent; PRELUDE THERAPEUTICS, INCORPORATED; LUENGO, Juan; LIN, Hong; (0 pag.)WO2018/160855; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 6299-85-0, 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. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Example 55; N-hydroxy-2-(hydroxyamino)-6-(4-(pyridin-3-ylethynyl)phenyl)pyrimidine-4- carboxamide, trifluoroacetic acid salt; A. Methyl 2-chloro-6-(4-(pyridin-3-ylethynyl)phenyl)pyrimidine-4-carboxylate; Methyl 2,6-dichloropyrimidine-4-carboxylate (0.5 g, 2.4 mmol), 3-((4-(5,5-dimethyl- l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)pyridine (0.35 g, 1.2 mmol, Method 2), K2CO3 (0.33 g, 2.4 mmol) and [l,4-bis(diphenylphospino)butane]palladium(II) dichloride (0.073 g, 0.12 mmol) were combined in dioxane (3 mL)/water (1 mL), purged with Argon and heated to 150 0C in the microwave. The reaction was stirred for 30 min. LC-MS after 30 minutes indicates reaction is complete as a mixture of ester and acid. The reaction mixture was diluted with water, neutralized with IN HCl, and extracted three times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and evaporated. The solid was dissolved in MeOH and trimethylsilyldiazomethane (2.4 mL, 4.8 mmol) was added. LC-MS after 15 minutes indicated formation of the methyl ester was complete. The reaction mixture was diluted with water and extracted three times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and evaporated to a solid (0.2Og, 23.7% yield). LC-MS: [M+H]+ 350 Mass: calculated for Ci9Hi2ClN3O2, 349.77

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BENENATO, Kerry, Ellen; CHOY, Allison, Laura; HALE, Michael, Robin; HILL, Pamela; MARONE, Valerie; MILLER, Matthew; WO2010/100475; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 705-24-8, 4,6-Dichloro-2-(trifluoromethyl)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, 705-24-8, blongs to pyrimidines compound. Recommanded Product: 4,6-Dichloro-2-(trifluoromethyl)pyrimidine

To 4,6-dichloro-2-(trifluoromethyl)pyrimidine (300 mg 1.38 mmol) in Dioxane (3 ml) was added ammonia solution (1 ml). The reaction was heated under microwave activation, at 100C for 20 min. After cooling, excess solvent was evaporated under reduced pressure. The obtained residue was taken to the next step without further purification. LC/MS: m/z 198 (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,705-24-8, its application will become more common.

Reference:
Patent; HELMHOLTZ-ZENTRUM FUeR INFEKTIONSFORSCHUNG GMBH; AHMED, Ahmed S. A.; EMPTING, Martin; HAMED, Mostafa; HARTMANN, Rolf W.; HAUPENTHAL, Joerg; HASTERKAMP, Thomas; KAMAL, Ahmed A. M.; MAURER, Christine K.; ROeHRIG, Teresa; SCHUeTZ, Christian; YAHIAOUI, Samir; ZENDER, Michael; (128 pag.)WO2020/7938; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 2915-16-4, 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 2915-16-4 as follows.

Example 90; [4- (4, 6-Diphenylpyrimidin-2-yl) -phenyl]methanol; A mixture of 2-chloro-4, 6-diphenylpryimidine, 0.79g (2.96 mmol), 4- (hydroxylmethyl)phenylboronic acid, 0.45g (2.96 mmol), Pd (PPh3) 4, 342mg (0.296 mmol), in 2 mL of toluene and EPO ImL of methanol was heated to obtain a clear solution. To the solution was added 2mL of 4.0M aq. Na2CO3. The reaction mixture refluxed for lbetah at 70 C. The mixture was cooled to room temperature and diluted with 10OmL ethyl acetate. The organic layer was washed with water, sat. aq. NaCl, and dried (MgSO4) . After the solution was concentrated, the residue was recrystallized with Et2O-Heptane (1:1) to afford the desired product in 0.38g (38%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2915-16-4, its application will become more common.

Reference:
Patent; THE INSTITUTES FOR PHARMACEUTICAL DISCOVERY, LLC; WO2006/55725; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine, 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, name: 2-Methanesulfonyl-4,6-dimethoxypyrimidine, blongs to pyrimidines compound. name: 2-Methanesulfonyl-4,6-dimethoxypyrimidine

EXAMPLE 1 Preparation of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene (Compound No. 104) A mixture comprising 2.1 g of 4-formyl-5-hydroxy-3-methylbenzothiophene, 2.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.8 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 70 C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 3.1 g (yield: 86%) of the desired compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US5616537; (1997); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 160199-05-3, 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.160199-05-3, name is 2,4-Dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, molecular formula is C10H4Cl2N2S, molecular weight is 255.1232, as common compound, the synthetic route is as follows.

70.0 g (274.4 mmol) of Intermediate B, 33.5 g (274.4 mmol) of phenylboronic acid, 94.8 g (686.0 mmol) of potassium carbonate, and 15.9 g (13.7 mmol) of tetrakis (triphenylphosphine) palladium (0) were added to 800 mE of 1 ,4-dioxane and 400 mE of water in a 2000 mE flask, and the mixture was heated under a nitrogen flow for 24 hours at 50 C. The obtained mixture was added to 3000 mE of methanol, and a solid crystallized therein was filtered, dissolved in monochlorobenzene, filtered with silica gel/Celite, and then, recrystallized with methanol afier removing an appropriate amount of an organic solvent to obtain Intermediate 13-2-1 (59.4 g, yield of 73%). calcd. C16H9C1N2S: C, 64.75; H, 3.06; Cl, 11.95; N, 9.44; 5, 10.80; found: C, 64.70; H, 3.02; Cl, 11.93; N, 9.40; 5, 10.73.

The chemical industry reduces the impact on the environment during synthesis 160199-05-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAMSUNG SDI CO., LTD.; KANG, Dong Min; KIM, Youngkwon; KIM, Changwoo; YU, Eun Sun; LEE, Byoungkwan; LEE, Hanill; JUNG, Sung-Hyun; JEONG, SooYoung; JUNG, Ho Kuk; (72 pag.)US2018/26205; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia