Day: July 19, 2021

Synthetic Route of 4212-49-1 ,Some common heterocyclic compound, 4212-49-1, molecular formula is C6H8N2O2, 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.

N, N-DIISOPROPYLETHYLAMINE (195 mL, 0.86 mol) (Aldrich) was added slowly to a mixture of 5-ethyl uracil (52.3 g, 0.37 mol) (from Example LC, suprn) and phosphorous oxychloride (150 mL, 1.61 mol) (Aldrich) with external cooling in a cold water bath. The mixture was heated at reflux for 3.8 hours and cooled to room temperature. Mixture was then poured into ice (300 g). Ethyl acetate (100 mL) was added and mixture stirred at 20 C for 30 minutes with cooling in an ice-water bath. The resulting mixture was filtered through CELITEE and the filtrate extracted with ethyl acetate-hexanes (1: 1,3 X 300 mL). The combined organic layers was washed with water (250 mL), dried over sodium sulfate, filtered and concentrated to dryness. This residue was dissolved in ethyl acetate- hexanes (1 : 1) and filtered through TLC grade silica gel and eluting with the same solvent. The filtrate was concentrated to dryness to give 2,4-dichloro-5-ethyl-pyrimidine. (Yield 56.3 g, 85.2%).

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. 4212-49-1, 5-Ethyluracil, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/41821; (2004); 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. 32779-37-6, name is 2,5-Dibromopyrimidine, molecular formula is C4H2Br2N2, 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. Formula: C4H2Br2N2

Example 73(S)-4-(4-(5-(2,2,2-Trifluoroethoxy)pyrimidin-2-ylamino)phenethyl)-4,5-dihydrooxazol-2-aminea) 5-Bromo-2-(2,2,2-trifluoro-ethoxy)-pyrimidineTo sodium hydride (303 mg) under an argon atmosphere at 0 C. was added dropwise 2,2,2-trifluoroethanol (775 mul) and the mixture was then stirred at RT for 90 min. A solution of 2,5-dibromopyrimidine (1.5 g) in DMF (8 ml) was then added and stirring continued at RT for 2 hours. The reaction mixture was poured into ice (50 mL) and extracted with EtOAc (2×50 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to afford 5-bromo-2-(2,2,2-trifluoro-ethoxy)-pyrimidine (790 mg, 49%) as a yellow oil which was used in the next step without further purification. MS (EI): 258 ([{81Br}M]+), 256 ([{79Br}M]+), 189 ([{81Br}M-CF3]+), 187 ([{79Br}M-CF3]+).

With the rapid development of chemical substances, we look forward to future research findings about 32779-37-6.

Reference:
Patent; Nettekoven, Matthias; Norcross, Roger; Polara, Alessandra; US2012/108609; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 49844-90-8, 4-Chloro-2-(methylthio)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, 49844-90-8, blongs to pyrimidines compound. Recommanded Product: 49844-90-8

Bromo trimethylsilane (23 mL, 174.31 mmol) was addedto a solution of 4-chloro-2-methylsulfanylpyrimidine (2.9 g 25 mmol) inacetonitrile (240 mL).The mixture was stirred for 30 h at 40C. The reactionwas monitored by TLC. After cooling to room temperature, NaHCO3saturated solution (250 mL) was added and the product was extracted with AcOEt.The organic layer was dried over Na2SO4, filtered, andevaporated under reduced pressure. The crude residue was purified bychromatography on silica gel using dichloromethane-ethyl acetate (9:1).Evaporation of the eluent in vacuum gave the desired compound in 96% yield(4.66 g) as colorless oil. Litt 1H NMR (CDCl3): delta 2.56(s, 3H, SCH3), 7.16 (d,1H, J = 5.2 Hz, H-5pyrimidine),8.26 (d, 1H, J = 5.2 Hz, H-6pyrimidine).13CNMR (CDCl3): delta 2.56 (s, 3H, SCH3),7.16 (d, 1H, J = 5.2 Hz, H-5pyrimidine),8.26 (d, 1H, J = 5.2 Hz, H-6pyrimidine).HPLC:Rt = 3.11min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,49844-90-8, its application will become more common.

Reference:
Article; Bendjeddou, Lyamin Z.; Loaec, Nadege; Villiers, Benoit; Prina, Eric; Spaeth, Gerald F.; Galons, Herve; Meijer, Laurent; Oumata, Nassima; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 696 – 709;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 934524-10-4, 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.934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C13H9Cl2N3O2S, molecular weight is 342.2, as common compound, the synthetic route is as follows.

A solution of 2,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.580 mmol), 3-aminobenzamide (83 mg, 0.61 mmol) and triethylamine (0.200 mL, 1.44 mmol) in dioxane (5 mL) was stirred at 1100C for 20 h. It was concentrated in vacuo. After the residue was acidified with HOAc ( 1 mL), it was purified by HPLC to give 3-(2-chloro-7-tosyl-7H- pyrrolo[2,3-d]pyrimidin-4-ylamino)benzamide (85 mg).

The chemical industry reduces the impact on the environment during synthesis 934524-10-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2009/131687; (2009); A2;,
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. 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C13H9Cl2N3O2S, 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. COA of Formula: C13H9Cl2N3O2S

Example 116; 2-[(2-{[1-(lambda/,lambda/-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-c/]pyrimidin-4-yl)amino]-6-fluoro-lambda/-methylbenzamide; Step A/Intermediate D4: 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7/-/-pyrrolo[2,3- c/]pyrimidin-4-yl}amino)-6-fluorobenzoic acid; A slurry of 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (50 g, 146 mmol) and 2-amino-6-fluorobenzoic acid (27.2 g, 175 mmol) (for instance from Acros Organics, Belgium) in iPrOH (1200 ml.) and 30 ml. of DIEA was heated to reflux. After 1 h, the solution turned a clear brown color, at which time about 450 ml_ of solvent were removed via distillation. The remaining mixture was treated with DIEA (90 ml.) and heated to reflux for 16 hours. The reaction mixture was then further concentrated by distilling more solvent off (400 ml. over 4 hours), then continued heating at reflux overnight. The resulting mixture was cooled to room temperature and concentrated under reduced pressure to obtain a thick oil which was diluted with EtOAc (1.3 L), then sequentially washed with a 1 N HCI solution (2×500 ml_), and a saturated NaHCOs solution (500 ml_). Further dilution of the separated organic layer with a saturated NaCI solution (500 ml.) led to the formation of a thick precipitate. The entire mixture was filtered and the solid was washed with Et2O. The solid was dried overnight in a vacuum oven at 60 0C to obtain 2-({2-chloro-7-[(4- methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid as a yellow solid (61.63 g, 92%). 1H NMR (400 MHz, DMSO-d6) delta ppm 2.37 (s, 3 H), 6.67 (d, J=3.85 Hz, 1 H), 6.71 – 6.81 (m, 1 H), 7.31 (td, J=8.33, 6.04 Hz, 1 H), 7.48 (d, J=8.24 Hz, 2 H), 7.74 (d, J=4.03 Hz, 1 H), 7.98 (d, J=8.42 Hz, 2 H), 8.36 (d, J=8.24 Hz, 1 H); ESIMS (M+H)+ = 461.06.

With the rapid development of chemical substances, we look forward to future research findings about 934524-10-4.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/20990; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10132-07-7, 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 10132-07-7, name is 4-Amino-2,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

N-tert-Butoxycarbonylpiperidinyl-4-methylamine (5.0 g) was slowly added to a stirred solution of 2,4-dichloro-6-aminopyrimidine (5.7 g) in 1-pentanol (20 mL). The solution was stirred at 120 C. for 12 hours. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/9) to give Intermediate 224-I (3.6 g) in a 45% yield. Intermediate 224-I (2.4 g) was then dissolved in CH2Cl2 (80 mL) and 20% TFA/CH2Cl2 (20 mL) was added. The solution was stirred at room temperature overnight. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (21% NH3 (aq)/MeOH=1/19) to afford Intermediate 224-II (1.5 g) in a 90% yield. Intermediate 222-III (3.3 g) prepared in Example 222 was added to a solution of Intermediate 224-II (1.9 g) in MeOH (40 mL). The mixture was stirred at 60 C. for 12 hours. NaBH4 (0.3 g) was then added at 0 C. After the mixture was stirred for 1 hour, an aqueous solution of NH4Cl (10%, 10 mL) was added. The mixture was extracted with EtOAc, dried over anhydrous MgSO4, and filtered. The solution thus obtained was then concentrated. The resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/1) to afford Intermediate 224-III (1.5 g) in a 40% yield. N1-Morpholine-N1-piperazine ethane (370 mg) was added to Intermediate 224-III (300 mg) in 1-pentanol (1 mL). The mixture was stirred at 120 C. for 12 hours. After the solution was concentrated, the residue was treated with water and extracted with CH2Cl2. The organic layer was separated and concentrated. The resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/9) to afford Intermediate 224-IV (281 mg) in a 70% yield. A solution of 20% TFA/CH2Cl2 (3 mL) was added to a solution of Intermediate 224-IV (281 mg) in CH2Cl2 (2 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 224 (200 mg) in a 85% yield. Compound 224 was then treated with 1 M HCl (4 mL) in CH2Cl2 (2 mL) for 0.5 hours. After the solvents were removed, the residue was treated with ether and filtered to give hydrochloride salt of Compound 224. CI-MS (M++1): 544.4.

According to the analysis of related databases, 10132-07-7, the application of this compound in the production field has become more and more popular.

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

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 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine

The 4,4 ‘ – (6-chloro-pyrimidine -2,4-diyl) two morpholine (301 mg, 1 . 06mmol), 7-bromo-8 – (trifluoromethyl) – 3,4-dihydro -2H-pyrido [3,2-b] [1,4] oxazine (200 mg, 0 . 71mmol),were taken and then duplex pinacone borate (350 mg, 1 . 38mmol), cesium fluoride (500 mg, 3 . 3mmol), palladium acetate (20 mg, 0 . 09mmol) and butyl b (1-adamantyl) diphenylphosphinobiphenyl (64 mg, 0 . 18mmol), were sequentially added to the toluene and methanol (4 ml, 1:1) in the mixed solvent, and added to the above mentioned solution, under nitrogen protection,at 70 C oil bath for 1 hour. After the reaction, concentrating, separating TLC (petroleum ether: ethyl acetate = 1:2), to obtain the title compound (45 mg, yield 14%).

With the rapid development of chemical substances, we look forward to future research findings about 10244-24-3.

Reference:
Patent; Shandong Xuan Bamboo Pharmaceutical Technology Co., Ltd.; Wu, Yong qian; (49 pag.)CN105461714; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 57489-77-7, 5,7-Dichloropyrazolo[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, Computed Properties of C6H3Cl2N3, blongs to pyrimidines compound. Computed Properties of C6H3Cl2N3

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%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57489-77-7, 5,7-Dichloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

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

Related Products of 4318-56-3, 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. 4318-56-3, name is 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C5H5ClN2O2, 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.

3-Methyl-6-chloro uracil (12 g, 76 mmol),Compound 3 (17.2 g, 80 mmol) and K2CO3 (10 g,80 mmol) in DMSO (100 mL) was stirred for 2 h and the reaction was diluted with water and extracted with EtOAc. The organic phase was dried over MgSO4 and the solvent was removed. Purification by column chromatography gave 4,13.2 g (60% yield).

According to the analysis of related databases, 4318-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Institute of Pharmaceutical Industry; China Pharmaceutical Industry Research Institute; Chen, Wu; Liu, Xiangkui; Ji, Zhongde; Zhu, Xueyan; Yuan, Zhedong; (10 pag.)CN105418580; (2016); 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.3001-72-7, name is 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine, molecular formula is C7H12N2, molecular weight is 124.1836, as common compound, the synthetic route is as follows.Safety of 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine

General procedure: The p-nitrophenyl carbonate derivative (0.3 g) was dissolved in AR grade THF (5 mL) at room temperature and DBU or DBN (2 equiv) was added. The temperature of the reaction mixture was raised to 60 C and stirring was continued for 1 h. After completion, the reaction mixture was extracted with ethyl acetate (2 × 30 mL), the organic layer washed with saturated NaHCO3 solution, water, brine and dried over anhydrous Na2SO4. Thesolvent was evaporated and the crude compound was purified by column chromatography

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3001-72-7, 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Vangala, Madhuri; Shinde, Ganesh P.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2086 – 2092;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia