Pyrimidines

Reference of 1211522-68-7, 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. 1211522-68-7, name is 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of ethanol (0.227 g, 4.93 mmol) in THF (60 mL) was added sodium hydride(0.591, 14.78 mmol) in ice bath. After 20 mi 4,6-dichloro-3-methyl-1H-pyrazolo-[3,4-d]-pyrimidine (Ig, 4.93 mmol) was added. The reaction mixture was gradually warmed to room temperature and then stirred overnight. Then, the mixture was diluted with water (20 mL), concentrated to remove solvent and diluted with ethyl acetate (220 mL). The organic layer was washed with water (60 mL x2), dried over Na2SO4, filtered and concentrated. The crudewas used in next step without further purification. Yield: 86%.LCMS: 213 [M+H]. tR 2.775 mins. (LCMS condition 1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1211522-68-7, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DING, Xiao; LIU, Qian; SANG, Yingxia; STASI, Luigi Piero; WAN, Zehong; ZHAO, Baowei; EDGE, Colin Michael; WO2015/113452; (2015); 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 85989-61-3, name is 5,7-Dichloroimidazo[1,2-c]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 85989-61-3

5,7-Dichloroimidazo[1,2-f]pyrimidine (100 mg, 0.5 mmol) and 3-amino-5-methyl pyrazole (52 mg, 0.5 mmol) were stirred in ethanol (1 ml) at 60 C. for 15 minutes. Alternatively, the pyrimidine and the pyrazole can be reacted in DMF at 100-150 C. for 15-30 minutes. The solvent was evaporated and the residue purified by flash chromatography using 1:1 EtOAc:Hexane then 1:10 MeOH/DCM. Evaporation of the solvent revealed 7-chloro-N-(5-methyl-1H-pyrazol-3-yl)imidazo[1,2-f]pyrimidin-5-amine (100 mg, 75%). 1H NMR (400 MHz, DMSO) delta 10.54 (s, 1H) 8.37 (s, 1H) 7.57 (s, 1H) 7.07 (s, 1H) 6.48 (s, 1H) 2.28 (s, 3H). [M+H] calc’d for C10H9ClN6, 249; found, 249.

With the rapid development of chemical substances, we look forward to future research findings about 85989-61-3.

Reference:
Patent; Dong, Qing; Hosfield, David J.; Paraselli, Bheema R.; Scorah, Nicholas; Stafford, Jeffrey A.; Wallace, Michael B.; Zhang, Zhiyuan; US2006/84650; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 31462-58-5, 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 31462-58-5, name is 5-Iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 10.1 (general route) N- 1 -(4-((4-(Pyrimidin-5-yloxy)phenyl)ethynyl)phenyl)propan-2-yl)acetam28.1 mg (0.14 mmol) 5-iodopyrimidine, 40.0 mg (0.14 mmol) N-(1 -(4-((4-hydroxy- phenyl)ethynyl)phenyl)propan-2-yl)acetamide (176.1 ), 1 .30 mg (0.07 mmol) Cul, 1 .9 mg (0.14 mmol) Nu, Nu-dimethylglycine hydrochloride and 58.7 mg (0.18 mmol) CS2CO3 are added to 1 ml_ dioxane. The reaction mixture is stirred at 90C for 2 h then filtered through a plug of silica gel and washed with DMF. The filtrate is purified by HPLC (MeOH/H20/TFA).C23H21 N3O2 (M= 371 .4 g/mol)ESI-MS: 372 [M+H]+ Rt (HPLC): 2.22 min (method M)

According to the analysis of related databases, 31462-58-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ROTH, Gerald Juergen; FLECK, Martin; HEINE, Niklas; KLEY, Joerg; LEHMANN-LINTZ, Thorsten; NEUBAUER, Heike; NOSSE, Bernd; WO2012/28676; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 186519-92-6, 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 186519-92-6, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 1. 4-Chloro-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide. To a flask was added 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (200 mg, 1.01 mmol), dimethyl amine (82.5 mg, 1.01 mmol) and CH3CN (2 mL). After 10 min, HATU (476 mg, 1.21 mmol) and DIEA (0.44 mL, 2.43 mmol) was added. The reaction mixture was stirred at rt for 2 hrs and then poured into water/DCM. The layers were separated and the organic extract washed with water, brine and dried (Na2SO4). The solvent was removed to give the crude, which was purified by chromatography (silica, MeOH/DCM, 0 to 10%) to give 4-chloro-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (100 mg, 44%). LC/MS (M+H) 225.1

According to the analysis of related databases, 186519-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thorarensen, Atli; Brown, Matthew Frank; Casimiro-Garcia, Agustin; Che, Ye; Coe, Jotham Wadsworth; Flanagan, Mark Edward; Gilbert, Adam Matthew; Hayward, Matthew Merrill; Langille, Jonathan David; Montgomery, Justin Ian; Telliez, Jean-Baptiste; Unwalla, Rayomand Jal; US2015/158864; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 69696-37-3, 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 69696-37-3, name is 5-Bromo-2,4-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

g) methyl 3-((3-carbamoyl-7-(2,4-dimethylpyrimidin-5-yl)quinolin-4-yl)amino)-5- isopropoxybenzoate. A mixture of methyl 3-((7-bromo-3-carbamoylquinolin-4- yl)amino)-5-isopropoxybenzoate (300 mg, 0.655 mmol) bis(pinacolato)diboron (183 mg, 0.720 mmol), potassium acetate (225 mg, 2.291 mmol), [1 , 1 – bis(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane adduct (26.7 mg, 0.033 mmol) and 1 ,4-dioxane (3 ml.) was heated at 1 10 C for 45 minutes in a microwave reactor. Cesium carbonate (427 mg, 1 .309 mmol), 5- bromo-2,4-dimethylpyrimidine (0.045 ml_, 0.393 mmol), [1 ,1 – bis(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane adduct (26.7 mg, 0.033 mmol), and water (1 ml.) were added and the mixture heated again in a microwave reactor at 1 10 C for 1 hour. LCMS indicated formation of the desired product. The mixture was filtered and purified by reverse-phase preparative HPLC (ODS, acetonitrile/0.03% aqueous ammonia) to afford the title compound (150 mg, 47%). LCMS (ES+) m/e 486 [M+H]+.

According to the analysis of related databases, 69696-37-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROWN, Kristin, K.; CHAI, Deping; DODSON, Christopher, S.; DUFFY, Kevin, J.; SHAW, Antony, Nicholas; WO2013/96151; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3270-97-1, 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 3270-97-1 as follows.

(Essigsaeure=acetic acid) To a stirred solution of 7.0 g (0.05 mol) 6-methoxy-2,4-diaminopyrimidine in 100 ml acetic acid (10% conc. in water) at 50-60 C. was added dropwise over a period of 30 min a solution of 4.55 g (0.07 mol) sodium nitrite in 20 ml water. The solution was stirred at this temperature for a further 30 min and then stirred at room temperature overnight. The filtrate was filtered off with suction, washed with water and dried. 5-Nitroso-2,4-diamino-6-methoxypyrimidine (7.80 g, 92%) was obtained as a violet solid. m.pt.: 250 C. (dec.) 1H-NMR (300 MHz, d6-DMSO): delta=4.04 (s, 3 H, 6-OMe), 7.79 (s,1H, NH2), 7.85 (s,1H, NH2), 8.01 (s,1H, NH2), 10.10 (s, 1H, NH2). 13C-NMR (125 MHz, d6-DMSO): delta=54.5 (6-OMe), 140.0 (5-C), 151.2 (2-C), 163.8 (4-C), 171.4 (6-C).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3270-97-1, its application will become more common.

Reference:
Patent; Gebert, Antje; Giesa, Helmut; Koenen, Annika; US2015/209257; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 31462-58-5 ,Some common heterocyclic compound, 31462-58-5, molecular formula is C4H3IN2, 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.

Zinc powder (0.12 g, 1.8 mmol) was added to a dry flask purged with nitrogen. Dry DMF (1.0 ml) was added followed by iodine (43 mg, 0.2 mmol). The solution changed from colourless to yellow and then back to colourless. Methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3- lodopropanoate (0.20 g, 0.60 mmol) was added, followed by iodine (43 mg, 0.2 mmol). The solution was stirred at ambient temperature, with an exotherm observed. To this solution was added Pd2(dba)3(28 mg, 0.04 mmol), SPhos (24 mg, 0.12 mmol) and 5-iodopyrimidine (0.33 g, 1.6 mmol). The RM was stirred at rt under nitrogen for 18 h. The RM was filtered twice and then purified by FCC (silica, EtOAc / hexane) to give the desired product. Y = 80 %MS ES+: 282

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31462-58-5, its application will become more common.

Reference:
Patent; NODTHERA LIMITED; HARRISON, David; WATT, Alan Paul; BOUTARD, Nicolas; FABRITIUS, Charles-Henry; GALEZOWSKI, Michal; KOWALCZYK, Piotr; LEVENETS, Oleksandr; WOYCIECHOWSKI, Jakub; (161 pag.)WO2018/167468; (2018); A1;,
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Pyrimidine – Wikipedia

Application of 87591-84-2, 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. 87591-84-2, name is 2-(Chloromethyl)-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, molecular formula is C10H9ClN2O, 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.

[0400] To a solution of I -(2-methoxyphenyl)-5-(thiophen-2-yl)- 1 H-imidazole-2-thiol (50.0 mg, 0.17 mmol) in acetone (2 mL) was added 2-(chloromethyl)-8-methyl-4H- pyrido[l,2-a]pyrimidin-4-one (40 mg, 0.19 mmol) and K2C03 (71 rng, 0.51 mmol). Then the mixture was warmed to 60 C and stirred until the reaction was completed (2hrs). Aftet cooling to room temperature, the reactant was filtered and the filtrate was concentrated to dryness in vacuum. The residue was diluted with EA (5 rnL) and the suspension was washed with aqueous 5% NaOH (5 mL), brine (5 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by Prep-TLC (PE/EA = 1/1) to give 2-[ I -(2-methoxy-phenyl)-5-thiophen-2-yl- I H-imidazol-2-ylsu lfanylmethyl]-7-methyl- pyrido[1,2-a]pyrimidin-4-one (20 mg, yield: 25%) as a yellow solid. [0401] ?HNMR (300 MHz, DMSO-d6): = 8.77 (s, 1H), 7.85 (dd, J= 9.0 Hz, 1.8 Hz,IH), 7.61-7.48 (m, 2H), 7.39 (s, lH), 7.36 (dd, J 8.0 Hz, 1.1 Hz, 1H), 7.27-7.16 (in, 2H),7.00 (t, 1=7.5 Hz, lH), 6.92 (dd, J 5.0 Hz, 3.8 Hz, lH), 6.80 (dd, J 5.0 Hz, 1.1 Hz, IH),6.34 (s, IH), 4.21 (s, 2H), 3.66 (s, 3H), 2.39 (s, 3H). MS: m/z 461.1 ( M+H).

According to the analysis of related databases, 87591-84-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; SMITH, Layton, H.; (113 pag.)WO2015/184011; (2015); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 52854-14-5, 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 52854-14-5, name is 4-Chloro-6-methoxy-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

The above product (3.50 g, 18.5 mmol) and 3′-aminobiphenyl-2-carbonitrile (prepared according to the procedure described in WO 02/38568) (3.23 g, 16.6 mmol) were dissolved in triethylamine (9. 32 g, 92.3 mmol) and dimethylsulfoxide (10 ml) and heated at 90C for 18 h. The mixture was allowed to cool to ambient temperature then poured onto water (150 ml) and extracted with ethyl acetate (2 x 300 ml). The organic fractions were combined, washed with water (3 x 75 ml) and brine (50 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give a brown solid. The brown solid was triturated with diethyl ether (50 ml), filtered, washed with diethyl ether (2 x 10 ml) and left to air dry, which gave 3′- (1-methyl-5-nitro-6-oxo-1, 6-DIHYDROPYRIMIDIN-4-YLAMINO) biphenyl-2-carbonitrile (2.24 g, 38%) as a yellow solid

According to the analysis of related databases, 52854-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/41826; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 890094-38-9, 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine, 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, Product Details of 890094-38-9, blongs to pyrimidines compound. Product Details of 890094-38-9

Compound (3a) (90.9 g, 0.420 mol), tetrahydrofuran (840 mL, abs.), Pt/C 5% (9.0 g, 42 mmol) and vanadyl acetylacetonate (4.5 g, 16 mmol) are added in a Parr apparatus and shaken under a hydrogen pressure of 50 psi at 20 C. to 40 C. for several hours until the reduction of the nitro group is complete (TLC control:silica gel, CH_EE=1:1). The catalyst is removed and the solvent is evaporated under reduced pressure. The crude product is dissolved in a mixture of tetrahydrofuran (100 mL) and isopropanol (120 mL) and transferred into a three necked flask. Trimethylchlorosilane (54 ml) is added dropwise and the hydrochlorid precipitates. The suspension is stirred for 16 hours. The precipitate is suction filtered and dried. Yield: 54.8 g (59% of theory) of compound (4a) as brown crystalline solid.

The synthetic route of 890094-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/329803; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia