Pyrimidines

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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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Electric Literature of 10397-13-4 ,Some common heterocyclic compound, 10397-13-4, molecular formula is C8H9Cl2N3O, 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.

Reference Example 2 6-Chloro-2-morpholin-4-vH4,5′]bipyrimidinyl-2′- ylamine (Intermediate B)Intermediate Al (140 mg, 0.60 mmol) and 2-aminopyrimidine-5-boronic acid pinacol ester (1.0 equiv., 83mg) were taken up in acetonitrile (3ml). To this were added sodium carbonate (3 equiv., 191mg) as a solution in water (ImI) and PdCl2(PPh3)2 (0.05 equiv.). The reaction mixture was heated in microwave at 14O0C for 30 min. Purification using SCX-2 cartridge, flash chromatography and diethyl ether trituration gave 6-chloro-2-morpholin-4-yl-[4,5′]bipyrimidinyl-2′-ylamine (53mg). The following compound was also isolated from the reaction mixture by flash chromatography purification: 2′-Mthetaphiholin-4-yl-[5,4′;6l,5″]terpyrimidine-2,2″-diamine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10397-13-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; WO2009/66084; (2009); A1;,
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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 83410-16-6, name is 4-Chloro-5-iodo-2,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H6ClIN2

Reference Example 94-Chloro-2,6-dimethyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine4-Chloro-2,6-dimethyl-5-iodopyrimidine and 4-ethynyl-alpha,alpha,alpha-trifluorotoluene were reacted in toluene in the presence of dichlorobis(triphenylphosphine)palladium, cuprous iodide and triethylamine while stirring under room temperature to heating to obtain a target substance. The target substance was subjected to e.g., proton nuclear magnetic resonance spectrometry (1H-NMR) and mass spectrometry (MS) and confirmed as the titled compound. Furthermore, MS measurement result is shown.Mass spectrum: 311,313.

With the rapid development of chemical substances, we look forward to future research findings about 83410-16-6.

Reference:
Patent; Nishio, Tetsuya; US2011/319618; (2011); A1;,
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Related Products of 5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

2-(isopropylsulfonyl)phenylamine (9.96 g, 50 mmol) was weighed and dissolved in N,N-dimethylformamide(DMF, 100 mL), to which sodium hydride (NaH, 2.4 g, 100 mmol) was slowly added on an ice bath and stirred for 0.5 h.A solution of 2,4,5-trichloropyrimidine (11.0 g, 60 mmol) dissolved in 20 mL of DMF was slowly added dropwise on anice bath. After the addition, the mixture was reacted overnight at room temperature, washed with water, and extractedwith ethyl acetate. After drying and concentration, the crude material was purified by column chromatography to give awhite solid 1-1 (6.9 g, 40%). MS(ESI): m/z 346.0 (M + H)+. 1H NMR (400 MHz, CDCl3) delta 10.07(s, 1 H), 8.63 (d, J = 8.0Hz, 1 H), 8.30 (s, 1 H), 7.92 (d, J = 7.4 Hz, 1 H), 7.73 (t, J = 7.4 Hz, 1 H), 7.33 (t, J = 7.0 Hz, 1 H), 3.22 (heptet, J = 6.0Hz,1 H), 1.32 (d, J = 6.0 Hz, 6 H). 13C NMR (100 MHz, CDCl3) delta 157.8, 156.3, 155.6, 137.3, 135.2, 131.4, 124.5, 124.2,122.7, 115.2, 56.1, 15.3.

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 5750-76-5, 2,4,5-Trichloropyrimidine.

Reference:
Patent; Precedo Pharmaceuticals Co., Ltd.; LIU, Jing; LIU, Qingsong; JIANG, Taoshan; WANG, Aoli; WU, Jiaxin; WU, Hong; QI, Ziping; CHEN, Yongfei; ZOU, Fengming; WANG, Wenchao; ZHAO, Zheng; WANG, Li; WANG, Beilei; (75 pag.)EP3392245; (2018); A1;,
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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. 16462-27-4, name is 2,4-Diaminopyrimidine-5-carbonitrile, the common compound, a new synthetic route is introduced below. Formula: C5H5N5

To a suspension of 2,4-diaminopyrimidine-5-carbonitrile (2) (0.41 g, 2 mmol) in MeOH (20 mL) was added Nickel (0.13 g, 2 mmol) under H2, and the mixture was at 25 C stirred for 24 h. Then the reaction mixture was filtered, the filtrate was removed under reduced pressure and the residue was dissolved in water, then the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to give 2,4-diaminopyrimidine-5-carbaldehyde (3) (0.22 g, 80% yield) as a white solid.

The synthetic route of 16462-27-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Wenhua; Yao, Xue; Huang, Zhenghui; Mao, Fei; Guan, Longfei; Tang, Yun; Jiang, Hualiang; Li, Jian; Huang, Jin; Jiang, Lubin; Zhu, Jin; Chinese Chemical Letters; (2019); p. 250 – 254;,
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