Category: pyrimidines

Reference 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.

Example 4b: Preparation of acetyl-N-(2.6-dichloropyrimidin-4-yl)hvdroxylamine (DCAP-Ac)2,6-Dichloropyrimidin-4-amine (DCAP, 20 g, 121.95 mmol) was suspended in acetic anhydride (400 mL, 4.27 mol, 35 molEq), and the suspension was heated to reflux. The obtained solution was stirred at reflux for 3.5 hours. The resulting reaction mixture was then cooled, concentrated to dryness in vacuo and the remaining acetic anhydride was removed by evaporation with toluene portions. The residue was dissolved in ethyl acetate (333 mL) and water (333 mL) and pH was adjusted to 7 by addition of 10% NaHC03. The organic layer was washed with saturated NaCl solution, and then evaporated to dryness. The residue was dissolved in acetic anhydride (cca 200 mL) and stirred at 0-5 C for 2 h. The precipitate that formed was filtered off and dried 5h / 40 C / 10 mbar.Yield: 18.34 (68%) of acetyl-N-(2,6-dichloropyrimidin-4-yl)hydroxylamine (DCAP-Ac). Purity (HPLC): 100 area %.

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 10132-07-7, 4-Amino-2,6-dichloropyrimidine.

Reference:
Patent; ASSIA CHEMICAL INDUSTRIEW LTD.; TEVA PHARMACEUTICALS USA, INC.; ?EPELJ MAJER, Maja; KRIZMANIC, Irena; ?EPAC, Dragan; WO2012/170647; (2012); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 105806-13-1, 4,6-Dichloro-5-fluoro-2-methylpyrimidine, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Part A: 4-Chloro-6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methylpyrimidine. To a solution of (3R)-1 ,3-dimethylpiperazine dihydrochloride (Example 63) (5.88 g, 31.4 mmol) in dichloromethane (126 mL) was added N,N-diisopropylethylamine (18.1 1 mL, 104 mmol), and 4,6-dichloro-5-fluoro-2-methylpyrimidine (5.69 g, 31.4 mmol). The solution was heated at 35 0C and stirred for 3 days. The solution was cooled to room temperature, diluted with DCM (100 mL), and washed with sat. aq. NaHCOs (100 mL). The aqueous phase was extracted with a fresh portion of DCM (50 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude 4-chloro-6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2- methylpyrimidine (9.60 g, >100 % yield) as a brown oil that was used without further purification. LCMS: (M+H)+: 258.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105806-13-1, 4,6-Dichloro-5-fluoro-2-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
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. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Methanesulfonyl-4,6-dimethoxypyrimidine

Add (10mmol) salicylaldehyde, (10mmol) 4,6-dimethoxy-2-methylsulfonylpyrimidine, (20mmol) potassium carbonate powder, and 30ml DMF into a 100ml three-necked flask equipped with a reflux condenser. Gradually heat to 60C, stir the reaction for 1 to 3 hours, and track the reaction to the end by TLC.Stop the reaction, transfer the reaction system to 100ml of water while it is hot, and stir it fully to precipitate a white or light yellow solid, with a yield of 92%, mp 91-92C, without purification, and directly used in the next reaction.

The synthetic route of 113583-35-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xi’an Modern Chemical Institute; Wang Wei; Wang Lieping; Li Bingbo; Zhang Xiaoguang; Liu Kangyun; Ning Binke; Xue Chao; (10 pag.)CN111269223; (2020); A;,
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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.1208170-17-5, name is 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C7H6ClN3S, molecular weight is 199.66, as common compound, the synthetic route is as follows.name: 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile

General procedure: A mixture of 3a,b (2.86 mmol), 4-methoxyaniline (0.36 g,2.88 mmol) and anhydrous K2CO3 (0.4 g, 5.76 mmol) inEtOH (15 ml) was heated under reflux for 5 h. It was thencooled, filtered and the filtrate was concentrated to half itsvolume. The obtained precipitate was filtered and crystallizedfrom EtOH-H2O (3:1 v/v).4-(4-Methoxyanilino)-6-methyl-2-(methylthio)-pyrimidine-5-carbonitrile (4a) Yield 71%; mp 158-160 C; IR v/cm-1:3300 (NH), 2214 (C?N), 1614 (C=N), 1604 (C=C-Ar),1293, 1134 (vas and vs C-O-C); 1H NMR (CDCl3, 60 MHz)delta/ppm: 7.49 (d, 2H, Ar-Hs, o- to NH-Ar, J = 12.6 Hz), 7.21(s, br, 1H, NH), 6.90 (d, 2H, Ar-Hs, o- to OCH3, J = 12.0Hz), 3.83 (s, 3H, OCH3), 2.58 (s, 3H, S-CH3), 2.50 (s, 3H,CH3); EIMS m/z 286 (M+., 100), 271 (33), 270 (25), 238(13); Anal. Calcd. for C14H14N4OS: (286.35): C, 58.72; H,4.93; N, 19.72. Found: C, 58.97; H, 4.98; N, 19.57.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1208170-17-5, 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Farghaly, Ahmed M.; AboulWafa, Omaima M.; Elshaier, Yaseen A. M.; Badawi, Waleed A.; Haridy, Haridy H.; Mubarak, Heba A. E.; Medicinal Chemistry Research; vol. 28; 3; (2019); p. 360 – 379;,
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Pyrimidine – Wikipedia

Related Products of 18592-13-7, 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 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

6-Chloromethyl uracil (500 mg, 3.1 mmol) was dissolved in THF (50 mL) and the solution was treated with 4-methoxybenzyl alcohol (860 mg, 6.2 mmol), triphenylphosphine (2.45 g, 9.3 mmol) and diisopropylazodicarboxylate (1.26 g, 6.2 mmol). The reaction was allowed to stir overnight at room temperature. The mixture was then poured over water (75 mL) and was extracted with ethyl acetate (3*50 mL). The combined organic extracts were dried over Na2SO4, filtered and reduced. Compound 28a was isolated and purified by normal phase column chromatograpy (silica gel, 20% EtOAc/heptane-100% EtOAc/heptane). M+ (ES+)=401.1.

According to the analysis of related databases, 18592-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Coats, Steven J.; Dyatkin, Alexey B.; He, Wei; Lisko, Joseph; Miskowski, Tamara; Ralbovsky, Janet L.; Schulz, Mark; US2008/269225; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 58347-48-1 ,Some common heterocyclic compound, 58347-48-1, molecular formula is C10H10ClN3O2, 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.

To a solution of ethyl 7-chloro-5-methylpyrazolo[l,5-a]pyrimidine-3-carboxylate (1.0 g, 4.18 mmol) in toluene (10 mL) was added (Bu3Sn)20 (5.0 g, 8.36 mmol). The reaction mixture was stirred at 120 C for 2 days, and concentrated in vacuo. The residue was dissolved in EtOAc (10 mL), and basified with sat. aHC03solution (10 mL) to pH~8-9. The aqueous phase was separated and acidified with 6N HC1 (10 mL) to pH~5. The solution was extracted with EtOAc (10 mL x 3). The organic phases were dried over anhydrous Na2S04, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (PE/EA; 1 : 1) to give 7-chloro-5-methylpyrazolo[l,5-a]pyrimidine-3- carboxylic acid (230 mg, 26%) as a white solid. LC-MS m/z: 211.0 [M+H]+, Purity (214 nm): >97%, tR= 1.23min.

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. 58347-48-1, Ethyl 7-chloro-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 33097-11-9, 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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, molecular formula is C6H4Cl2N2OS, 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.

General procedure: To a stirred solution of aldehyde 1 (1.0mmol, 1equiv) in 3mL DMF was added enamine 2 (1.15equiv) followed by addition of a few drops of satd ethereal HCl. (0027) Except for 6d: Mixture was stirred at ambient temperature for period of time indicated in Table 1. After removing of solvent (50C/5 Torr) the residue was stirred with water (10mL) for 1h, crystals were filtered and dried at 110C/5 Torr to give compound 6 with purity?94%. Recrystallization from DMF can be used for purification, if necessary. (0028) For 6d: After stirring for 20h the additional portion of enamine 4d (0.15equiv) was added and the mixture was left at ambient temperature for 4 days. After removing of solvent (50C/5 Torr) the residue was dissolved in CHCl3 (30mL), washed with water, satd NaHCO3 and brine. Compound 6d was isolated using column chromatography on silica (EtOAc-nHexane 1:1, Rf?0.25).

According to the analysis of related databases, 33097-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chizhova, Maria E.; Bakulina, Olga Yu.; Ivanov, Alexander Yu.; Lobanov, Pavel S.; Dar’in, Dmitrii V.; Tetrahedron; vol. 71; 36; (2015); p. 6196 – 6203;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 55583-59-0, 2,5-Diamino-4,6-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, Formula: C4H4Cl2N4, blongs to pyrimidines compound. Formula: C4H4Cl2N4

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (1.00 g, 5.59 mmol),4- (N, N-Dimethylamino) phenylboronic acid(0.922 g, 5.5 9 mmol),Sodium carbonate (2.96 g, 27.9 mmol),To a solution of tetrakis (triphenylphosphine) palladium (0) (0.323 g, 0.560 mmol) in toluene (56 mL) was added ethanol (14 mL) and distilled water (14 mL) at room temperature, and then under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (16 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (20 mL).Thereafter, the whole organic layer was combined, saturated aqueous sodium chloride solution (20 mL) was added thereto, the mixture was stirred and washed, anhydrous sodium sulfate was added to the separated organic layer for dehydration, and the filtrate after filtration was concentrated under reduced pressure .The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4-Chloro-6- (4- (dimethylamino) phenyl) pyrimidine-2,5-diamine(0.727 g, 49% yield).

The synthetic route of 55583-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
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Pyrimidine – Wikipedia

Application of 5466-43-3 ,Some common heterocyclic compound, 5466-43-3, molecular formula is C7H6Cl2N2, 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.

Morpholine (0.32 mL, 3.7 mmol) was added to a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.5 g, 2.65 mmol) in anhydrous ethanol (5 mL) and stirred at a temperature in the range of 65 C. to 85 C. for 10 to 16 hours. Thereafter, the mixture was concentrated under reduced pressure and the crude was diluted with anhydrous ether. After standing at a temperature in the range of 5 C. to 10 C. for 2 hours, the precipitated solid was filtered and washed with ether. The solid was recrystallized from ethyl acetate to afford the title compound as a pale yellow solid (0.54 g, 86% yield).1H NMR (CDCl3, 300 MHz): delta 4.10-3.94 (m, 4H), 3.90-3.76 (m, 4H), 3.36-3.20 (m, 2H), 3.10-2.90 (m, 2H), 2.29-2.12 (m, 2H).LC-MSD (ES+): (m/z) 240 [(M+H)+, 100].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144731; (2010); A1;,
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Pyrimidine – Wikipedia

Reference of 84905-80-6, 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.84905-80-6, name is 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

(i) Production of {4-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]phenyl}methanol 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (307 mg) was dissolved in N,N-dimethylformamide (2 mL), potassium carbonate (304 mg) was added, and the mixture was stirred at room temperature for 30 min. 4-Hydroxymethylbenzyl chloride (377 mg) was added, and the mixture was stirred at room temperature for 16 hrs. After diluting with water (30 mL), the mixture was extracted with ethyl acetate/tetrahydrofuran (3:1, 80 mL*2). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20 ? 0:100) to give the title compound (383 mg) as a powder. 1H-NMR(CDCl3) delta: 2.15 (1H, br s), 4.69 (2H, d, J= 4 Hz), 5.71 (2H, s), 6.76 (1H, m), 7.06 (2H, d, J= 8 Hz), 7.34 (2H, d, J= 8 Hz), 7.50 (1H, d, J= 3 Hz), 8.69 (1H, s).

Statistics shows that 84905-80-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1752457; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia