Tag: M.W:100-200

Related Products of 100644-67-5, 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. 100644-67-5, name is 4-Methoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine. A new synthetic method of this compound is introduced below.

A suspension of 6-amino-4-methoxy-1H-pyrazolo[3.4-d]pyrimidine (purine base A, 9.0g, 54.5 mmol, 1.0 eq) and a catalytic amount of ammonium sulfate in hexamethyldisilazane(HMDS, 150 mL) was refluxed for 6 h. The excess hexamethyldisilazane was removed byevaporation under reduced pressure, and the residue was dissolved in 1,2-dichloroethane (200 mL).l-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (ribose I) (35.7 g, 70.8 mmol, 1.3 eq) was added at roomtemperature. The reaction mixture was cooled to 0 C, and trimethylsilyl trifluoromethanesulfonate(TMSOTf, 29.6 mL, 163.5 mmol, 3.0 eq) was added dropwise for 30 min with stirring. The reactionmixture was stirred at room temperature overnight. Upon completion of the reaction as monitoredby TLC, the mixture was diluted with dichloromethane (200 mL) and washed with saturated sodiumbicarbonate solution. The aqueous layer was extracted with dichloromethane. The combinedorganic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.The resulting residue was purified by column chromatography to afford 10.0 g main product N9-isomer 24 as a white solid in 30.3% yield with an HPLC purity of 96%; Rf = 0.3 (petroleum ether¡Àethylacetate = 1:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100644-67-5, 4-Methoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine, and friends who are interested can also refer to it.

Reference:
Article; Ren, Hang; An, Haoyun; Tao, Jingchao; Molecules; vol. 24; 5; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1119280-68-0 , The common heterocyclic compound, 1119280-68-0, name is 2-Chlorothieno[3,2-d]pyrimidine, molecular formula is C6H3ClN2S, 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.

2-Methoxythieno[3,2-i/]pyrimidine (17).; To a solution of 16 (146 mg, 0.86 mmol) in MeOH (20 mL) was added NaOMe (130 mg, 2.41 mmol). The solution was heated at reflux for 37 h. An additional 1.4 equiv of NaOMe (65.0 mg) was added after 24 h (Note: The reaction was complete in 7 h with comparable yields when 4.2 equiv of NaOMe were added at the start of the reaction). The reaction mixture was cooled to room temperature, quenched with 1 N aq. HC1 (2.0 mL), and extracted with DCM (4 x 10 mL). The combined organic layers were washed with H20 (10 mL), dried (MgS04), and concentrated under reduced pressure to provide 17 (125 mg, 88%) as an off-white solid: Mp 167.0-168.5 C (DCM); IR (ATR, neat) 3071, 3025, 2917, 1558, 1528, 1478, 1379, 1295, 1249, 1031, 796, 677 cm”1; 1H NMR (DMSO- 6, 300 MHz) delta 9.30 (d, 1 H, J= 0.6 Hz), 8.45 (d, 1 H, J= 5.4 Hz), 7.47 (dd, 1 H, J= 5.4, 0.7 Hz), 3.96 (s, 3 H); 13C NMR (DMSO-d6, 75 MHz) delta 163.4, 162.4, 154.8, 139.9, 124.8, 122.9, 54.6; MS (EI) m/z 166 (M+, 29), 84 (100); HRMS (EI) m/z calcd for C7H6N2OS 166.0201, found 166.0201.

The synthetic route of 1119280-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; WIPF, Peter; WANG, Qiming, Jan; WO2012/78859; (2012); A2;,
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. 696-45-7, name is 4-Amino-6-methoxypyrimidine, the common compound, a new synthetic route is introduced below. name: 4-Amino-6-methoxypyrimidine

A sealed tube was charged with 6-methoxypyrimidin-4-amine (23 mg, 0.19 mmol), methyl (1S, K or lR,45)-4-[5-(6-bromo-4-methylpyridin-2-yl)-l,3-thiazol-2-yl]-4- hydroxy-2,2-dimethylcyclohexanecarboxylate (80 mg, 0.18 mmol), XantPhos (16 mg, 0.03 mmol), cesium carbonate (119 mg, 0.36 mmol), and palladium(II) acetate (4 mg, 0.02 mmol). The vial was evacuated and backfilled with argon (3x). Fully degassed dioxane (0.7 mL) was added, the tube was sealed, and stirred at 90 ¡ãC overnight. The reaction was then cooled to room temperature, diluted with methanol, and absorbed onto 1.2 g of silica. Purification via silica gel chromatography (ethyl acetate/hexanes) afforded a 6: 1 mixture of (1R,4,S or lR,45)-l-(5-{6-[(6- methoxypyrimidin-4-yl)amino]-4-methylpyridin-2-yl} -l,3-thiazol-2-yl)-5,5-dimethyl-2- oxabicyclo[2.2.2]octan-3-one : methyl (15″,4R or lR,45)-4-hydroxy-4-(5- {6-[(6- methoxypyrimidin-4-yl)amino]-4-methylpyridin-2-yl} -l,3-thiazol-2-yl)-2,2- dimethylcyclohexanecarboxylate.; A 6: 1 mixture of (R,4S or lR,45)-l-(5- {6-[(6-methoxypyrimidin-4- yl)amino]-4-methylpyridin-2-yl} -l,3-thiazol-2-yl)-5,5-dimethyl-2-oxabicyclo[2.2.2]octan-3-one : methyl (1,S,4R or lR,45)-4-hydroxy-4-(5- {6-[(6-methoxypyrimidin-4-yl)amino]-4- methylpyridin-2-yl} -l,3-thiazol-2-yl)-2,2-dimethylcyclohexanecarboxylate (70 mg, 0.16 mmol) was taken up in methanol (2 mL) and sodium hydroxide (1M in water, 0.31 mL, 0.31 mmol) was added. The reaction was capped and stirred at 85 ¡ãC overnight. The reaction was then cooled to room temperature and acidified with 0.15 mL of 2 M aqueous hydrochloric acid. A significant amount of precipitate formed. The reaction was then diluted with water, pH3 phosphate buffer, and 5 mL of ethyl acetate and stirred for 5 minutes. The resulting slurry was filtered. The filter cake was washed with water and diethyl ether and then dried in vacuo to afford (1,S,4R or lR,45)-4-hydroxy-4-(5- {6-[(6-methoxypyrimidin-4-yl)amino]-4-methylpyridin-2-yl}-l,3- thiazol-2-yl)-2,2-dimethylcyclohexanecarboxylic acid as a white solid. MS ESI calcd. for C23H28 504S [M+H]+ 470, found 470.

The synthetic route of 696-45-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ANTHONY, Neville, J.; ANDRESEN, Brian, M.; NORTHRUP, Alan, B.; CHILDERS, Kaleen, K.; DONOFRIO, Anthony; MILLER, Thomas, A.; LIU, Yuan; MACHACEK, Michelle, R.; WOO, Hyun Chong; SPENCER, Kerrie, B.; ELLIS, John Michael; ALTMAN, Michael, D.; ROMEO, Eric, T.; GUAY, Daniel; GRIMM, Jonathan; LEBRUN, Marie-Eve; ROBICHAUD, Joel, S.; WANG, Liping; DUBOIS, Byron; DENG, Qiaolin; WO2014/176210; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 49844-90-8, 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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine. A new synthetic method of this compound is introduced below.

A mixture of 4-chloro-2-(methylthio)pyrimidine (102.6 g, 0.639 mol), 3-phenyl- 1 H-pyrazole-4-carbaldehyde (100.0 g, 0.581 mol), potassium carbonate (160.5 g, 1.162 mol), and dimethylformamide (700.0 mL) was stirred at 40-50C for 2 hours. Purified water (1.6 L) was slowly added to the reaction mixture, which was then stirred at room temperature for 2 hours. The resulting solid was filtered and then dried in vacuo to obtain 154.0 g of the titled compound. (Yield: 8 1.4%)1H-NMR(400MHz, CDC13) oe 10.10(s, 1H), 9.20(s,1H), 8.65(d, 1H), 7.84-7.86(m, 2H), 7.67-7.71(m, 3H), 2.65(s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,49844-90-8, 4-Chloro-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; YUHAN CORPORATION; OH, Sang-Ho; KHOO, Ja-Heouk; LIM, Jong-Chul; LEE, Seong-Ran; JU, Hyun; SHIN, Woo-Seob; PARK, Dae-Gyu; PARK, Su-Min; HWANG, Yoon-Ah; (37 pag.)WO2019/22485; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 38275-55-7, Adding some certain compound to certain chemical reactions, such as: 38275-55-7, name is 5-Fluoropyrimidine-2-carbonitrile,molecular formula is C5H2FN3, 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 38275-55-7.

Intermediate 9N-( 1 -(5-Fluoropyrimidin-2-yl)vinyl)acetamide; 5-Fluoropyrimidine-2-carbonitrile (Intermediate 8, 1.0 g, 8.1 mmol) in THF (10 ml) was added a solution of MeMgBr (3.3 ml, 9.75 mmol) in ether drop wise at 0 0C. After addition, the reaction was warmed to room temperature, stirred at room temperature for 1 hour and then diluted with DCM (10 ml). Acetic anhydride (1.23 ml, 13.0 mmol) was added in one portion. The reaction was stirred at room temperature for 1 hour and 40 0C for 1 hour. Saturated sodium bicarbonate solution (10 ml) was added and extracted with EtOAc (2×20 ml). The combined organic was dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography (hexane : EtOAc = 2.5 : 1) to give the title compound as a white solid (0.38 g, 26%). 1H NMR (400 MHz) 9.34 (s, IH), 8.95 (s, 2H), 6.25 (s, IH), 6.03 (s, IH), 2.11 (s, 3H). MS: Calculated: 181; Found: [M+H]+ 182.

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. 38275-55-7, 5-Fluoropyrimidine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/135786; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5604-46-6, 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.5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, molecular formula is C5H3Cl2N3O, molecular weight is 192.0028, as common compound, the synthetic route is as follows.

A solution of methyl 1-hydrazinyl-1, 2, 3, 4-tetrahydronaphthalene-1-carboxylate hydrochloride (0.7 g, 2.7 mmol) and 2-amino-4, 6-dichloropyrimidine-5-carbaldehyde (0.52 g, 2.7 mmol) in MeCN (30 ml) was stirred at rt overnight and then heated to 70. The reaction mixture was stirred at 70 for 1h. After completion, the mixture was filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography with PE: EtOAc (5: 1) to afford product (0.66 g, 68%) as a light yellow solid. MS: M/e 358 (M+1) +.

The chemical industry reduces the impact on the environment during synthesis 5604-46-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); 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 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 287714-35-6

To the reaction mixture of methyl 2-chloropyrimidine-5-carboxylate (2.5 g, 14.487 mmol) in THE (10 mL), methyl magnesium chloride (14.487 mL, 43.463 mmol) was added drop wise at 0C and the mixture was stirred at rt for 30 mm. After completion of reaction the reaction mixture was poured into 50 mL of IN HCI and extracted with ether. The ether layer was washed with water, dried over anhydrous Na2SO4 and concentrated. The resulting crudeproduct was purified by flash chromatography (Elutant: 55-60% EtOAc in pet ether) to afford title compound (pale yellow solid). 1H NMR (400 MHz, DMSO-d6): 6 1.48 (5, 6H), 5.51 (5, IH), 8.84 (5, 2H). LCMS: (Method A) 173.0 (M +H), Rt. 1.659 mm, 98.64% (Max).

With the rapid development of chemical substances, we look forward to future research findings about 287714-35-6.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 87253-62-1, 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 87253-62-1 as follows.

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,87253-62-1, its application will become more common.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 111196-81-7, Adding some certain compound to certain chemical reactions, such as: 111196-81-7, name is 2-Chloro-5-ethylpyrimidine,molecular formula is C6H7ClN2, 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 111196-81-7.

To a reaction flask was added compound18(700 mg, 2.19 mmol) and 2-chloro-5-ethylpyrimidine (621 mg, 4.37 mmol) in one-portion in the presence of anhydrous DMF. After stirring at room temperature for 5 min, to the resulting clear solution was added anhydrous K2CO3(453 mg, 3.28 mmol) in one-portion. The reaction flask immersed in a pre-heated oil-bath (90) and the reaction mixture was stirred at 90for 4 h and cooled to room temperature. To the reaction mixture at room temperature under vigorous stirring and H2O was added slowly dropwise over 30 min to give an off-white slurry. After the addition was finished, the resulting slurry was stirred at room temperature for additional 10 min. The precipitate was filtered and then rinsed with H2O (2 x 30 mL) and the precipitate was dissolved in EtOAc, and washed with H2O (2 x 30 mL). The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purifiedby silica gel column chromatography using 40% EtOAc in hexanes to afford compound19(680 mg, 73%).1H-NMR (CDCl3, 300 MHz) delta 9.87 (1H, s, CHO), 8.19 (2H, s, pyrimidine), 7.64 (2H, d,J= 6.9 Hz, Ar), 7.29 (1H, s, thiazole), 7.18 (1H, t,J= 6.9 Hz, Ar), 5.32 (2H, s, OCH2), 4.81 (2H, d,J= 6.0 Hz, CH2), 3.33 (1H, t,J= 12.3 Hz, CH), 3.25 (2H, t,J= 9.3 Hz, CH2), 2.46 (2H, q,J= 9.3 Hz, CH2), 2.19 (2H, d,J= 11.7 Hz, CH2), 1.79 (2H, dq,J= 12.0 Hz, 2.7 Hz, CH2), 1.22 (3H, t,J= 9.0 Hz, CH3).

According to the analysis of related databases, 111196-81-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Hyojin; Cho, Suk Joon; Yoo, Minjin; Kang, Seung Kyu; Kim, Kwang Rok; Lee, Hwan Hee; Song, Jin Sook; Rhee, Sang Dal; Jung, Won Hoon; Ahn, Jin Hee; Jung, Jae-Kyung; Jung, Kwan-Young; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5213 – 5220;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 65996-50-1, 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 65996-50-1 as follows.

(4) To 1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione (35.0g) was added aqueous 1N sodium hydroxide solution (231ml) and after stirring for a while, the mixture was concentrated in vacuo. The residue was subjected to azeotropic distillation with toluene. To the residue was gradually added phenylphosphonic dichloride (239g) and then the temperature of the mixture was raised to 180C, followed by stirring for 3 hours. Thereto was further gradually added phenylphosphoric dichloride (100g) and the mixture was stirred overnight. The reaction mixture was gradually poured into ice-water under stirring and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate solution, dried and concentrated in vacuo. To the residue was added ethyl acetate/ diisopropyl ether to give 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine as crystals (19.96g). APCI-MS (m/e): 188/190 (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,65996-50-1, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP1956009; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia