Month: August 2021

Reference of 10070-92-5, 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

EXAMPLE l N -[3-(cyclopentyloxy)phenyl]-2,2,2-trifluoro-N -(pyrimidin-5-ylmethyl)ethanesulfonamideDiisopropyl azodicarboxylate (0.45 mL, 2.3 mmol) was added dropwise to a stirred solution of 3-aminophenol (250 mg, 2.3 mmol), cyclopentanol (0.25 mL, 2.8 mmol), and triphenylphosphine (600 mg, 2.3 mmol) in tetrahydrofuran (1.4 mL) at 0 0C. After stirring for an additional 12hr at room temperature, the reaction mixture was rotovapped in vacuo to remove volatile solvents. The residue was directly purified via column chromatography on silica gel (eluting 5-50% EPO ethyl acetate/hexanes) to give 157 mg (40%) of [3-(cyclopentyloxy)phenyl]amine as red oil. To a solution of [3-(cyclopentyloxy)phenyl]-amine (157 mg, 0.89 mmol), pyrimidine aldehyde (96 mg, 0.89 mmol) and acetic acid (51 uL, 0.89 mmol) in dichloroethane 3.6 mL) was added sodium triacetoxyborohydride (283 mg, 1.3 mmol) at room temperature. The resulting mixture was stirred for an additional 2hr or until TLC indicated complete conversion. The reaction mixture was then rotovapped in vacuo to remove volatile solvents. The residue was directly purified via column chromatography on silica gel (eluting 15-100% ethyl acetate/hexanes) to give 200 mg (83%) of [3-(cyclopentyloxy)phenyl]- (pyrimidin-5-ylmethyl)amine as brown oil.A solution of 2,2,2-trifluoroethanesulfonyl chloride (0.1 ImL, l.Ommol) was added dropwise to a solution of [3-(cyclopentyloxy)phenyl](pyrimidin-5-ylmethyl)amine (200 mg, 0.74 mmol) in dichloroethane (2.8 mL) and pyridine (1.4 mL) at 00C. The reaction mixture was allowed to gradually warm to room temperature and then stirred at room temperature until TLC indicated completion of reaction. The solution was then rotovapped in vacuo to remove volatile solvents. The residue was directly purified via column chromatography on silica gel (eluting with 0-100% ethyl acetate/dichloromethane) to give N -[3-(cyclopentyloxy)phenyl]-2,2,2-trifluoro-N -(pyrimidin-5- ylmethyl)ethanesulfonamide as a solid. 1H NMR(CDCl3, 500MHz), delta 9.14 (s, IH), 8.61 (s, 2H), 7.29- 7.25 (m, IH), 6.87-6.85 (m, IH), 6.81-6.79 (m, IH), 6.72-6.71 (m, IH), 4.89 (s, 2H), 4.67-4.65 (m, IH), 3.88-3.83 (m, 2H), 1.90-1.61 (m, 8H). MS (ESI): 416 (M+ + H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10070-92-5, Pyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2006/49968; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 919116-36-2, 4-Chloro-2-(methylthio)-5-(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, Computed Properties of C6H4ClF3N2S, blongs to pyrimidines compound. Computed Properties of C6H4ClF3N2S

To a mixture of 4-(3-iodo-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazolo[3,4-b]pyridin-6- yl)-3-methylisoxazole (952 mg, 2.32 mmol), 4-chloro-2-(methylthio)-5- (trifluoromethyl)pyrimidine (637 mg, 2.78 mmol), and hexamethylditin (486 uL, 2.32 mmol) in toluene (13 mL), purged with nitrogen (5 min), was added Pd(PPh3)4 (268 mg, 232 umol), and the reaction mixture was stirred at 105 C until full conversion (24 h). The reaction mixture was poured into a freshly prepared solution of aqueous potassium fluoride (1.0 g in 50 mL), and stirred for 30 min. The resulting mixture was filtered on Celite pad, and the filtrate was extracted with ethyl acetate (3×30 mL). The organic layers were combined, washed with brine (30 mL), dried over anh. Na2S04, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc in hexanes, 10 to 70% gradient) to afford the title compound (529 mg, 1.11 mmol, 48% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,919116-36-2, 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SYROS PHARMACEUTICALS, INC.; MARINEAU, Jason J.; CHUAQUI, Claudio; CIBLAT, Stephane; KABRO, Anzhelika; PIRAS, Henri; WHITMORE, Kenneth Matthew; LUND, Kate-Lyn; (200 pag.)WO2019/143719; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 155-10-2, 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. 155-10-2, name is 4-Amino-2-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, 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.

Example 95 5-Fluoro-N2-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-ylmethyl]-pyrimidine-2,4-diamine EXAMPLE 95 was prepared from C-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-yl]-methylamine and 2-chloro-5-fluoro-pyrimidin-4-ylamine: MS (m+1)=394.5.

According to the analysis of related databases, 155-10-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Claiborne, Christopher F.; Butcher, John W.; Claremon, David A.; Libby, Brian E.; Liverton, Nigel J.; Munson, Peter M.; Nguyen, Kevin T.; Phillips, Brian; Thompson, Wayne; McCauley, John A.; US2002/165241; (2002); 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. 59950-53-7, name is 5-Aminopyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Aminopyrimidine-4-carboxylic acid

15 g of 5-aminopyrimidine-4-carboxylic acid was addedIn 200 ml of methanol,Add dropwise 10ml thionyl chloride, stirred at room temperature overnight, concentrated,Add 200 ml of toluene, concentrate,Get 18g 5-aminopyrimidine-4-carboxylate.

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, 59950-53-7, 5-Aminopyrimidine-4-carboxylic acid.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Bu Gonggaofamingren; (4 pag.)CN107176926; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, 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, SDS of cas: 26032-72-4, blongs to pyrimidines compound. SDS of cas: 26032-72-4

In the synthesis of intermediate 2,Using Intermediate 8 instead of Intermediate 1,Intermediate 10 was used instead of phenylboronic acid,The synthesis was carried out in the same manner. Under an argon gas flow,Intermediate 1 (11.9 g, 50 mmol) was added successively to the reaction vessel,Phenylboronic acid (7.9 g, 65 mmol),Tetrakis (triphenylphosphine) palladium (1.73 g, 1.5 mmol),Toluene 170 mL,Ethanol 30 mL,2M aqueous sodium carbonate solution (50 mL),And the mixture was heated under reflux for 8 hours.After the reaction solution was cooled to room temperature,The organic layer was separated,The organic solvent was removed by distillation under reduced pressure.The resulting residue was purified by silica gel chromatography,To give intermediate 2 (11.6 g, 49 mmol (yield 98%)).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; Mizuki, Yumiko; Ito, Hirokatsu; Haketa, Tasuku; Hayama, Tomoharu; Nishimura, Kazuki; Kawamura, Masahiro; Shibata, Mitsuru; (73 pag.)CN105408310; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 62802-42-0, 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.62802-42-0, name is 2-Chloro-5-fluoropyrimidine, molecular formula is C4H2ClFN2, molecular weight is 132.5235, as common compound, the synthetic route is as follows.

Preparation 115 N-[(4aR,7aS)-6-(5-Fluoropyrimidin-2-yl)-7a-phenyl-4,4-a,5,7-tetrahydropyrrolo[3,4d][1,3]thiazin-2-yl]benzamide A solution of N-[(4aR,7aS)-7a-phenyl-4-a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (250 mg, 0.629 mmol), 5-fluoro-2-chloropyrimidine (167 mg, 1.26 mmol), 1,4-dioxane (10 mL), and triethylamine (318 mg, 3.14 mmol) is stirred at 110 C. for 4 hours. The reaction is cooled, diluted with water and extracted with dichloromethane. The organic layers are combined, dried, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1) to give the title compound (0.217 g, 80%). ES/MS (m/e): 434 (M+H).

The chemical industry reduces the impact on the environment during synthesis 62802-42-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eli Lilly and Company; BECK, James Peter; GREEN, Steven James; LOPEZ, Jose Eduardo; MATHES, Brian Michael; MERGOTT, Dustin James; PORTER, Warren Jaye; RANKOVIC, Zoran; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR, Leonard Larry; US2013/261111; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 62802-38-4, 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.62802-38-4, name is 5-Bromo-2-fluoropyrimidine, molecular formula is C4H2BrFN2, molecular weight is 176.9745, as common compound, the synthetic route is as follows.

Step 3: A mixture of 1,3-dimethyl-1H-pyrazol-4-amine (453 mg, 4.66 mmol), 5- bromo-2-fluoropyrimidine (750 mg, 4.24 mmol) and DWA (1.62 mL, 21.8 mmol) in DM50 (5 mE) was heated with at 120 C for 2 h. The resulting mixture was cooled to it and quenched with water. The yellow solid was collected via filtration, washed with water, and dried in vacuum oven to give 5-bromo-N-(1,3-dimethyl-1H-pyrazol-4-yl)pyrimidin-2-amine (1.08 g, 99%). LC-MS (ESI) m/z 268, 270 (M+Hjb.

The chemical industry reduces the impact on the environment during synthesis 62802-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PLEXXIKON INC.; HOLLADAY, Mark W.; LIU, Gang; (267 pag.)WO2017/19804; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1193-21-1, 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 1193-21-1 as follows.

EXAMPLE 8 This example illustrates the preparation of (E)-methyl 2-[2-(4-fluoropyrimidin-6-yloxy)phenyl]-3-methoxypropenoate, an intermediate for the synthesis of compounds of the invention. A mixture of 4,6-dichloropyrimidine (6.50 g), sulphur tetrafluoride (20.8 g) and Arcton 113 (35 ml) was heated at 50 C. with stirring in a 100 ml Monel reactor for 3.3 hours. The temperature was increased to 100 C. over 25 minutes and maintained at 100 C. for a further 3 hours. The temperature was increased to 151 C. over 20 minutes and maintained at 151 C. for 3 hours. The vessel was then allowed to cool to room temperature. The reaction mixture was poured into saturated sodium hydrogen carbonate solution and extracted with dichloromethane. A sticky solid was observed at the interface and was removed by filtration. The layers were then separated. The organic layer was washed with water, and then distilled at atmospheric pressure to remove the dichloromethane. 4,6-Difluoropyrimidine was isolated by distillation in vacuo (50 C./100 mmHg) as a light yellow oil (400 mg; 7.3% yield); 1 H NMR delta: 6.61 (1H, s); and 8.69 (1H, s)ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-21-1, its application will become more common.

Reference:
Patent; Imperial Chemical Industries PLC; US5145856; (1992); A;,
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.302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, molecular weight is 394.2783, as common compound, the synthetic route is as follows.Safety of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

A mixture of 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methyl phenyl) thiazole- 5 -carboxamide compound of formula-2 (50 gm), 2-(piperazin-l-yl)ethanol compound of formula-3 (82.5 gm) & 1 ,2-propanediol (750 ml) is expelled with nitrogen for 30 minutes. N,N- diisopropylethylamine (43.6 ml) was added to the reaction mixture and heated the reaction mixture to 115-120C. Stirred the reaction mixture for 8 hours at the same temperature. Cooled the reaction mixture to 25-30C and stirred for 6 hours at the same temperature. Filtered the precipitated solid and washed with 1 ,2-propanediol. Methanol (1300 ml) was added to the obtained wet compound and heated the reaction mixture to 65-70C. Stirred the reaction mixture for 2 hours at the same temperature. Filtered the reaction mixture at 65-70C and washed with methanol. Cooled the filtrate to 25-30C and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with methanol and dried to get the title compound. Yield: 38 gm; HPLC Purity: 99.57%, 0.01% (N-Oxide impurity), 0.09% (Deshydroxyethyl dasatinib); PXRD pattern of the obtained compound depicted in figure-5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; MADHUSUDHAN, Gutta; SEETHA RAMA SARMA, Peri; KHALIL AHAMED, Mogal; (38 pag.)WO2017/2131; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10132-07-7 , The common heterocyclic compound, 10132-07-7, name is 4-Amino-2,6-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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 solution of piperidinyl-4-methylamine (3.6 g) and N-tert-butoxycarbonylimidazole (5.3 g) in toluene (80 mL) was stirred at 25 C. overnight. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/2) to give Intermediate 227-I (4.7 g) in a 70% yield. Intermediate 227-I (4.7 g) and Et3N (2.7 mL) in 1-pentanol (20 mL) was reacted with 2,4-dichloro-6-aminopyrimidine (5.4 g) at 120 C. for 12 hours. After the solvent was removed, the residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/9) to afford Intermediate 227-II (5.2 g) in a 70% yield. A solution of Intermediate 227-II (1.0 g) treated with 1 M HCl (20 mL) in CH2Cl2 (10 mL) was stirred at room temperature for 8 hours. After the solution was concentrated, the resultant residue was neutralization with NH4OH, and extracted with CH2Cl2. The organic layer was separated and concentrated. The residue thus obtained was purified by column chromatography on silica gel (using MeOH as an eluant) to afford Intermediate 227-III (636 mg) in a 90% yield. Intermediate 222-III (790 mg) prepared from Example 222 was added to a solution of Intermediate 227-III (450 mg) in MeOH (20 mL). The mixture was stirred at 25 C. for 2 hours. NaBH(OAc)3 (2.0 g) was then added at 25 C. for 12 hours. After the solution was concentrated, a saturated aq. NaHCO3 solution was added to the resultant residue. The mixture was then extracted with CH2Cl2. The organic layer was separated and concentrated. The residue thus obtained was purified by column chromatography on silica gel (using MeOH as an eluant) to afford Intermediate 227-IV (539 mg) in a 60% yield. N1-Morpholine-N1-piperazine ethane (240 mg) was added to a solution of Intermediate 227-IV (160 mg) in 1-pentanol (1 mL). The mixture was stirred at 120 C. for 8 hours. The solution was concentrated and the residue was purified by column chromatography on silica gel (EtOAc/MeOH=5/1) to afford Intermediate 227-V (85 mg) in a 40% yield. A solution of 20% TFA/CH2Cl2 (1 mL) was added to a solution of Intermediate 227-V (85 mg) in CH2Cl2 (1 mL). The reaction mixture was stirred for 8 hours at room temperature and concentrated by removing the solvent. The resultant residue was purified by column chromatography on silica gel (21% NH3 (aq)/MeOH=1/19) to afford Compound 227 (65 mg) in a 90% yield. Compound 227 was then treated with 1 M HCl (1 mL) in CH2Cl2 (1 mL) for 0.5 hour. After the solvents were removed, the residue was treated with ether and filtered to give hydrochloride salt of Compound 227. CI-MS (M++1): 544.4.

The synthetic route of 10132-07-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yen, Chi-Feng; Hu, Cheng-Kung; Chou, Ming-Chen; Tseng, Chen-Tso; Wu, Chien-Huang; Huang, Ying-Huey; Chen, Shu-Jen; King, Chi-Hsin Richard; US2006/281712; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia