Day: August 18, 2021

Synthetic Route of 4983-28-2, Adding some certain compound to certain chemical reactions, such as: 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine,molecular formula is C4H3ClN2O, 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 4983-28-2.

A combination of methanesulfonic acid-l-(3-ethyl-[l,2,4]oxadiazol-5-yl)piperidin-4- ylmethyl ester (Preparation 52, 440mg, 1.51mmol), 2-chloropyrimidin-5-ol (270mg, 1.81mmol) and potassium carbonate (417mg, 3.02mmol) in DMF (20mL) was heated to 100°C in a microwave reactor for 2 h. The reaction solvent was concentrated in vacuo and the resulting residue was dissolved in EtOAc. The solution was washed with 1M NaOH solution (x 2), brine, then dried (MgS04), before removal of the solvent in vacuo.Purification by column chromatography (DCM:MeOH, 95:5) afforded the title compound: 1H NMR deltaEta (400MHz , CDC13): 8.27 (s, 1H), 8.25 (s, 1H), 4.26 – 4.15 (m, 2H), 3.95 – 3.85 (m, 2H), 3.15 – 3.00 (m, 2H), 2.62 – 2.50 (m, 2H), 2.15 – 2.01 (m, 1H), 1.97 – 1.85 (m, 2H), 1.52 – 1.38 (m, 2H), 1.30 – 1.19 (m, 3H).

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. 4983-28-2, 2-Chloro-5-hydroxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROSIDION LIMITED; BARBA, Oscar; BELL, James, Charles; DUPREE, Tom, Banksia; FRY, Peter, Timothy; BERTRAM, Lisa, Sarah; FYFE, Matthew, Colin, Thor; GATTRELL, William; JEEVARATNAM, Revathy, Perpetua; KEILY, John; KRULLE, Thomas, Martin; MCDONALD, Russell, Walker; MORGAN, Trevor; RASAMISON, Chrystelle, Marie; SCHOFIELD, Karen, Lesley; STEWART, Alan, John, William; SWAIN, Simon, Andrew; WITHALL, David, Matthew; WO2011/147951; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 36082-50-5, 5-Bromo-2,4-dichloropyrimidine, 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, Safety of 5-Bromo-2,4-dichloropyrimidine, blongs to pyrimidines compound. Safety of 5-Bromo-2,4-dichloropyrimidine

f) Production of methyl-N-(5-bromo-2-chloropyrimidin-4-yl)-D-alaninate 22.8 g (100 mmol) of 5-bromo-2,4-dichloropyrimidine and 14.0 g (100 mmol) of D-alanic acid methyl ester hydrochloride are dissolved in 300 ml of THF and 75 ml of DMF. The ice-cooled batch is mixed with 33.5 ml (240 mmol) of triethylamine and then slowly heated to room temperature. After 48 hours, the solvent is drawn off in a rotary evaporator, and the remaining residue is purified by chromatography (hexane/ethyl acetate: 4:1 – 2:1). 25.5 g (86.1 – mmol, corresponding to 86% of theory) of the product is obtained. 1H-NMR (CDCl3): 8.2 (s, 1 H), 6.1 (d, 1 H), 4.8 (m, 1 H), 3.8 (s, 3H), 1.6 (d, 3H).

The synthetic route of 36082-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Aktiengesellschaft; EP1705177; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 10244-24-3, 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, 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: 10244-24-3, blongs to pyrimidines compound. SDS of cas: 10244-24-3

A solution of 40 g of 2,4-[bis-morpholino]-6-chloropyrimidine and 34 g of piperazine in 60 g of pyridine is heated at 100 for 24 h. The mixture is partitioned between methylene chloride and aqueous potassium carbonate. The organic phase is filtered through sodium sulfate and concentrated. The residue is chromatographed (methylene chloride to 4% methanol/1% ammonium hydroxide/methylene chloride) to give the title compound, NMR (CDCl3) 2.90, 3.50, 3.75, 3.80 and 5.10 delta.

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; Upjohn Company; US5099019; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 274693-26-4, 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. 274693-26-4, name is 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol. A new synthetic method of this compound is introduced below.

Under nitrogen, the reaction flask were added isopropylidene ticagrelor, N,N- diisopropylethylamine (2.30g, 17.8mmol) and tetrahydrofuran 10mL, stirring (1.00g, 1.78mmol) 5 C to clarification, cooled to -5 C ~ 0 C. 5ml of tetrahydrofuran was added dropwise to the reaction solution phosphorus oxychloride (2.72g, 17.7mmol), the reaction solution is controlled temperature 0 C~ 5 C, 10min dropwise addition, the reaction temperature 0 C ~ 5 C for 2h. Under nitrogen, the reaction solution was slowly added dropwise 20ml of methanol, 0 C ~ 5 C reaction 1h, warmed to 10 C~ 15 C reaction was continued for 1h. To the reaction was added dropwise 30ml of water, temperature 5 C ~ 15C, addition was complete, warmed to 25 C ~ 30 C reaction 1h. 60ml of ethyl acetate twice. The combined organic phase was washed with 30ml water and 30ml saturated brine the organic phase, the resulting organic phase was dried over anhydrous sodium sulfate 1g IH, suction filtered, the filtrate was distilled off under reduced pressure, to give as a white solid 1.01g, yield 90.11%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,274693-26-4, 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Hefei Medical Engineering Pharmaceutical Co., Ltd.; Hefei Enruite Pharmaceutical Co., Ltd.; Nanjing Medical Engineering Pharmaceutical Co., Ltd.; He Guangwei; Chu Zhaoxing; He Jianxun; Xu Qinlong; Ye Wenfeng; Li Jiaming; Xu Yungen; Wei Ping; Zhu Qihua; Wang Kui; Mo Jiajia; (16 pag.)CN108623629; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13223-25-1 , The common heterocyclic compound, 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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.

EXAMPLE 2 Preparation of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate (Compound No. 2) To 0.5 g of 60% sodium hydride, 50 ml of hexane was added, and subjected to decantation. Then, the mixture was suspended in 30 ml of dimethylformamide. To the dimethylformamide suspension, 1.9 g of ethyl 3-hydroxypicolinate was gradually added, and the 2.0 g of 2-chloro-4,6-dimethoxypyrimidine was added. The mixture was heated and stirred at a reaction temperature of from 130 to 140 C. for 4 hours. After cooling, the reaction solution was poured into water, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1.4 g of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate. (Yield: 40%, pale yellow liquid, refractive index nD20 =1.5389)

The synthetic route of 13223-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US4832729; (1989); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5305-40-8, 4,6-Dichloropyrimidine-5-carbaldehyde, 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, Recommanded Product: 5305-40-8, blongs to pyrimidines compound. Recommanded Product: 5305-40-8

4-Amino-6-chloropyrimidine-5-carbaldehyde (27) [0169] A solution of 7 M NH3 in MeOH (265 mL, 1.855 mol, 2.0 equiv) was added over 1.25 h to a solution of 4,6-dichloropyrimidine-5-carbaldehyde (163.7 g, 0.9301 mol) in toluene (3 L) at ambient temperature. The reaction temperature slowly increased from 20 to 26 C. and a yellow suspension formed. Mild cooling was applied to maintain the reaction temperature at below 26 C. The suspension was stirred at ambient temperature for 3.5 h before the solids were collected by filtration. The solids were washed with EtOAc (1 L). The filtrate was concentrated under reduced pressure, and the solids were triturated with toluene and n-heptane (2:1 v/v, 600 mL), filtered and dried to give 71.1 g of 4-amino-6-chloropyrimidine-5-carbaldehyde as a yellow solid. The original solid filtered from the reaction mixture contained additional amount of 4-amino-6-chloropyrimidine-5-carbaldehyde. The product was extracted from the filtered solid by stirring in EtOAc (1.25 L) for 1.5 h, filtering, then stirring in THF (750 mL) for 1 h and again filtering. Both EtOAc and THF filtrates were concentrated under reduced pressure, and the resulting solids were triturated with toluene and n-heptane (2:1 v/v, 450 mL), filtered and dried to give an additional 44.1 g of 4-amino-6-chloropyrimidine-5-carbaldehyde as a yellow solid. The combined yield of 4-amino-6-chloropyrimidine-5-carbaldehyde (115.2 g, 146.5 g theoretical) was 78.6%. 1H NMR (300 MHz, DMSO-d6) delta 10.23 (s, 1H), 8.71 (bs, 1H), 8.55 (bs, 1H), 8.39 (s, 1H) ppm; C5H4ClN3O (MW, 157.56), LCMS (EI) m/e 158 (M++H).

The synthetic route of 5305-40-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Liu, Pingli; Wang, Dengjin; Wu, Yongzhong; Cao, Ganfeng; Xia, Michael; US2014/256941; (2014); 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.138274-14-3, name is 5-(Benzyloxy)-2-chloropyrimidine, molecular formula is C11H9ClN2O, molecular weight is 220.66, as common compound, the synthetic route is as follows.HPLC of Formula: C11H9ClN2O

To a 50 mL single-mouth bottle was added 5-benzyloxy-2-chloro-pyrimidine 34b (0.21 g, 0.95 mmol), morpholine (1.0 mL, 11 mmol), water (1 mL) and potassium carbonate (0.27 g, 1.9 mmol) The resulting reaction solution was stirred at 100 C for 19 hours.After the reaction solution was cooled to room temperature, the reaction solution was adjusted to pH = 3 with hydrochloric acid (1 mol/L).The mixture was extracted with EtOAc (EtOAc) (EtOAc)The title compound 46a (0.25 g, yield 96%) obtained as white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,138274-14-3, 5-(Benzyloxy)-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Gu Zheng; Li Jianhao; Li Zheng; Wang Weihua; Tan Haoxiong; Wang Xuli; Cui Yunzeng; Xie Zeqiang; Zhang Yingjun; (101 pag.)CN109251166; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1337532-51-0, Adding some certain compound to certain chemical reactions, such as: 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine,molecular formula is C7H7BrN4, 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 1337532-51-0.

To a stirred solution of 3-benzyl-7-bromo-8-fluoroisoquinoline (0.13 g, 0.41 1 mmol, 1 equiv) in 1 ,4-dioxane (10 mL) was added bis(pinacolato)diboron (0.10 g, 0.41 1 mmol, 1 equiv), and potassium acetate (0.12 g, 1 .23 mmol, 3 equiv). The reaction mixture was degassed with N2 for 10 minutes. PdCl2(dppf)-CH2Cl2 adduct (0.0167 g, 0.02 mmol, 0.05 equiv) was added and the mixture was degassed with N2 for 5 minutes. The reaction mixture was stirred for 12 hour at 100 C in a sealed vessel. The reaction was cooled to room temperature. 5-bromo-7-methyl-7/-/-pyrrolo[2,3-c ]pyrimidin-4-amine (0.094 g, 0.41 1 mmol, 1 .0 equiv), saturated aqueous NaHC03 (3 mL) and PdCI2(dppf)-CH2Cl2 adduct (0.0167 g, 0.02 mmol, 0.05 equiv) was added and the reaction mixture was degassed with N2 for 5 minutes. The vessel was sealed and the reaction mixture was stirred for 8 hour at 100 C. The mixture was filtered through celite and the filtrate was evaporated to obtain crude product, which was purified by silica gel flash column chromatography. The compound eluted out in 3 % MeOH:DCM. The fractions containing product were evaporated to obtain 5-(3-benzyl-8-fluoroisoquinolin-7-yl)-7-methyl-7H^yrrolo[2,3-c ]pyrimidin-4-amine (0.012 g, 8 %) as an off-white solid. LCMS (ES) m/z = 384.2 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 3.76 (s, 3H), 4.26 (s, 2H), 6.13 (br.s., 2H), 7.19 (t, J=6.8 Hz, 1 H), 7.27 – 7.35 (m, 4H), 7.42 (s, 1 H), 7.70 (t, J=8.0 Hz, 1 H), 7.78 – 7.80 (m, 2H), 8.15 (s, 1 H), 9.41 (s, 1 H).

According to the analysis of related databases, 1337532-51-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (162 pag.)WO2018/15879; (2018); 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.51674-77-2, name is 4-Chloropyrido[3,2-d]pyrimidine, molecular formula is C7H4ClN3, molecular weight is 165.58, as common compound, the synthetic route is as follows.Product Details of 51674-77-2

Intermediate 9 (700 mg, 2.06 mmol), ethyl 1-piperazineacetate (0.5 g), «-BuOH (10 mL) and DIPEA (2 mL) were combined in a sealed tube and heated at 130C for 12 days. The reaction mixture was cooled, concentrated onto silica and purified by column chromatography (Si02, 0-100% EtOAc in isohexane). The resulting material, EtOH (7 mL) and 2M HC1 in Et20 (5 mL) were combined and stirred at r.t. for 3 days. The reaction mixture was concentrated to give a pale yellow solid. A portion of this material (50 mg), «-BuOH (6 mL), DIPEA (1 mL) and 4-chloropyrido[3,2-<%yrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated under microwave irradiation at 160C for 2 h. 15% NaOH solution (0.2 mL) was added to the reaction mixture, which was stirred at r.t. for 3 days. The mixture was concentrated to dryness and purified by preparative HPLC to give the title compound (38.1 mg) as a brown glass. 5H (DMSO-<¾) 8.93-8.85 (2H, m), 8.53 (IH, s), 8.49 (IH, s), 8.17 (IH, dd, J 8.46, 1.58 Hz), 7.90 (IH, dd, J 8.46, 4.25 Hz), 7.72 (IH, dd, J 8.91, 6.29 Hz), 7.30 (IH, t, J 9.11 Hz), 5.90-5.81 (IH, m), 3.76-3.65 (2H, m), 3.27 (2H, s), 3.25-3.17 (2H, m), 2.98-2.89 (2H, m), 2.88-2.79 (2H, m), 2.57 (3H, s), 1.64 (3H, d, J 6.69 Hz). LCMS (ES+) 476 (M+H)+, RT 2.43 minutes (Method 1) At the same time, in my other blogs, there are other synthetic methods of this type of compound,51674-77-2, 4-Chloropyrido[3,2-d]pyrimidine, and friends who are interested can also refer to it. Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2011/58108; (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.905856-70-4, name is 2-Bromo-5-iodopyrimidine, molecular formula is C4H2BrIN2, molecular weight is 284.88, as common compound, the synthetic route is as follows.Quality Control of 2-Bromo-5-iodopyrimidine

5) In a 250 ml three-necked flask, 0.03 mol of intermediate 4-4 was added under nitrogen protection.0.036 mol of 2-bromo-5-iodopyrimidine, 150 ml of toluene, stirred and mixed, and then added 0.045 mol of sodium t-butoxide.0.0015 mol Pd2 (dba) 3, 0.0015 mol of tri-tert-butylphosphine, heated to 115 C with stirring.The reaction was refluxed for 24 hours, and the spot plate was sampled, indicating that no intermediate 4-4 remained, and the reaction was complete;Naturally cooled to room temperature, filtered, and the filtrate was evaporated to dryness under reduced pressure and passed through a neutral silica gel column.Intermediate 4-5 was obtained with HPLC purity of 99.3%, yield 68.9%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,905856-70-4, 2-Bromo-5-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Tang Dandan; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (66 pag.)CN108203416; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia