Day: September 14, 2021

Electric Literature of 39906-04-2, Adding some certain compound to certain chemical reactions, such as: 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine,molecular formula is C5H5Cl2N3, 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 39906-04-2.

General procedure: A microwave vial was charged with the corresponding aniline (1 , 1 .0 mmol), the 4,6-dichloropyrimidine (2, 1 .0 mmol), isobutanol (2.5 mL) and 37% aqueous HCI (0.07 mL/mmol). The reaction vessel was sealed and heated in a microwave reactor at 150 C for 10-30 min. After cooling, the reaction mixture was worked up as indicated in each case. Following the general procedure, a microwave vial was charged with 5-amino- 4,6-dichloro-2-methylpyrimidine (200 mg, 0.48 mmol), 3-chloroaniline (50 muIota_, 0.48 mmol), isobutanol (1 .2 mL) and 37% aqueous HCI (36 muIota_). After cooling, the product was isolated by filtration and dried to obtain 120 mg (93%) of 3c as a brown solid. Mp: 239-241 C. MS (ES, positive mode): m/z 269 (M+H)+with a 2 CI isotopic pattern. 1 H NMR (DMSO-d6, 300 MHz): delta 2.33 (s, 3H, CH3), 6.38 (s, 2H, NH2), 7.05 (ddd, J = 8.0, 2.0, 0.8 Hz, 1 H, H-4′), 7.33 (pt, J = 8.1 Hz, 1 H, H-5′), 7.73 (ddd, J = 8.3, 2.0, 0.8 Hz, 1 H, H-6′), 7.99 (pt, J = 2.1 Hz, 1 H, H-2′), 9.1 1 (s, 1 H, NH).

According to the analysis of related databases, 39906-04-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; CONSEJO SUPERIOR DE INVESTIGACIONS CIENTIFICAS (CSIC); PEREZ PEREZ, Maria Jesus; GIGANTE MARTINEZ, Alba; CANELA GOMEZ, Maria Dolores; LEYSSEN, Pieter; NEYTS, Johan; WO2014/170368; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1722-12-9, 2-Chloropyrimidine, 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, 1722-12-9, blongs to pyrimidines compound. name: 2-Chloropyrimidine

Example 7 N-(1-Methyl-5-phenyl-1H-imidazol-2-yl)-3-phenyl-propionamide (90) To a solution of 2-chloropyrimidine (90a, 2.0 g, 17.5 mmol) in THF (25 mL) was added 40% CH3NH2(aq) (7.5 mL) at 0 C. The reaction mixture was stirred at 50 C. for 1.0 hour and then poured into saturated NaHCO3(aq) and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure to give N-methylpyrimidin-2-amine (90b).To a microwave vial containing a solution of N-methylpyrimidin-2-amine (90b, 290 mg, 2.7 mmol) in acetonitrile (5 mL) was added 2-bromo-1-phenylethanone (714 mg, 3.6 mmol). The vial was sealed and heated in a microwave reactor at 130 C. for 20 minutes and then cooled to room temperature. The reaction mixture was treated with hydrazine hydrate (0.65 mL, 13.3 mmol) and then heated in a microwave reactor at 100 C. for 5.0 minutes. The solution was poured into water and filtered the precipitate to give 1-methyl-5-phenyl-1H-imidazol-2-ylamine (90c).To a solution of 1-methyl-5-phenyl-1H-imidazol-2-amine (90c, 52.0 mg, 0.3 mmol) in pyridine (1.0 ml) was added 3-phenyl-propionyl chloride (60.7 mg, 0.36 mmol). The reaction mixture was stirred at room temperature for 16 hours, quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give N-(1-Methyl-5-phenyl-1H-imidazol-2-yl)-3-phenyl-propionamide (90) : 1H NMR (500 MHz, DMSO) delta: 7.16-7.48 (m, 10H), 6.87 (s, 1H), 3.42 (s, 3H), 3.07 (t, 2H), 2.92 (t, 2H). ESI-MS: 305.7 (M+H)+.Compounds 91 was synthesized in a manner similar to that describe above and its observed ESI-MS was 309.8 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1722-12-9, its application will become more common.

Reference:
Patent; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; US2012/172374; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 14161-09-2, Adding some certain compound to certain chemical reactions, such as: 14161-09-2, name is 2-(Methylsulfonyl)pyrimidine,molecular formula is C5H6N2O2S, 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 14161-09-2.

Example 124 3-(pyrimidin-2-yloxy)-5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazole Compound A (0.100 g, 0.34 mmol) and B (0.268 g, 1.69 mmol) were added to a 0.2-5 mL microwave tube. DMF (3 mL) was added. The mixture was stirred and microwaved at 120 C. for 30 min, and then filtered. The filtrate was purified by HPLC. The fractions from HPLC were combined, K2CO3 (0.5 g) were added, extracted with EtOAc. The organic solution was concentrated. The resultant material was filtered through a short silica gel column with 1% MeOH in EtOAc to afford the title compound (6.4 mg, 5%). 1H NMR (400 MHz, DMSO-d6) delta 8.74 (d, J=4.8 Hz, 2H), 8.03 (dd, J=9.0, 1.8 Hz, 1H), 7.95-7.88 (m, 2H), 7.83-7.75 (m, 2H), 7.45 (t, J=4.8 Hz, 1H), 7.44-7.39 (m, 2H). m/z: 374 (MH+)

According to the analysis of related databases, 14161-09-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Graupe, Michael; Lu, Yafan; Zablocki, Jeff A.; US2015/175560; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

Reference Example 7 A solution of 2,2-dimethyl-5-hydroxy-4-oxo-benzo-1,3-dioxin (8.0 g) in tetrahydrofuran was added dropwise during 0.25 hour to a stirred suspension of sodium hydride (1.75 g of 60%) under nitrogen. After 0.25 hour 4,6-dimethoxy-2-methylsulphonylpyrimidine (9.68 g) was added during 5 minutes and the mixture heated at reflux overnight. The cooled mixture was diluted with water, extracted (ether), dried (magnesium sulphate), evaporated and purified by chromatography on silica gel eluding with isohexane/ethyl acetate to give 5-(4,6-dimethoxypyrimidin-2-yl)oxy-2,2-dimethyl-4-oxo-benzo-1,3-dioxin (2.64 g).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine.

Reference:
Patent; Cramp, Michael Colin; Mack, Stephen Robert; Gingell, Michael; US2001/29239; (2001); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 14080-59-2, Adding some certain compound to certain chemical reactions, such as: 14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine,molecular formula is C6H3ClN2S, 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 14080-59-2.

4-Chlorothieno[2,3-d]pyrimidine (10) (5.80 g, 34.0 mmol) was dissolved in dry THF (300 mL) under nitrogen, cooled to -78 C, n-butyllithium (1.1 equiv, 23.4 ml, 1.6 M in hexane) was added and the mixture stirred at -78 C for 4 h. An excess of solid carbon dioxide was added and the mixture allowed to warm up to room temperature overnight. The solvents were removed under reduced pressure, and the remaining solid was suspended in water (300 mL). The suspension was filtered over a pad of celite and the clear solution was acidified with conc. HCl under stirring. The precipitating colourless crystals were collected by filtration and dried. 65% yield; colourless crystals; mp 195 C (decomp.); 1H NMR (300 MHz, DMSO-d6): delta 9.01 (s, 1H), 8.07 (s, 1H) ppm. MS (ESI+): 256 ([MH++CH3CN]+, 100; 35Cl), 215 ([M+H]+, 12; 35Cl). IR (KBr): nu 3442, 3091, 1724 cm-1. Anal. (C7H3ClN2O2S; 214.63): C, H, N.

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. 14080-59-2, 4-Chlorothieno[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Beckers, Thomas; Sellmer, Andreas; Eichhorn, Emerich; Pongratz, Herwig; Schaechtele, Christoph; Totzke, Frank; Kelter, Gerhard; Krumbach, Rebekka; Fiebig, Heinz-Herbert; Boehmer, Frank-D.; Mahboobi, Siavosh; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 125 – 136;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 287714-35-6 ,Some common heterocyclic compound, 287714-35-6, molecular formula is C6H5ClN2O2, 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.

2-Chloropyrimidine-5-carboxylic acid methyl ester (434mg, 2.33 mmol) was added to a stirring suspension of (2R)-2-amino-3-methyl-3-{[(2E)-3,7,11,15- tetramethylhexadec-2-en-1-yljsulfanyl}butanoic acid (ig, 2.33 mmol) and N,Ndiisopropylethylamine (1.2lmL, 6.99 mmol) in dioxane (lOmL) at room temperature and heated to 60C overnight. The reaction mixture is cooled to room temperature and washed once with brine. The reaction mixture is diluted with an additional 5mL of dioxane, followed by addition of 1M lithium hydroxide (lOmL) at room temperature and stirred overnight. The reaction mixture is diluted with ethyl acetate, washed with 10% w/v citric acid solution, then brine and dried over magnesium sulfate. The ethyl acetate is filtered and concentrated on a rotary evaporator to give the crude product as a yellow oil that is purified by flash chromatography using ethyl acetate in hexanes as the eluent to give the purified carboxylic acid as an off-white solid. The carboxylic acid was dissolved in ethanol, then solid sodium ethoxide was added until the pH reached 9. The resulting ethanolic suspension was centrifuged at 2000 rpm for 2 minutes. The ethanol was decanted and the ethanol wash was repeated twice more. Acetonitrile was then substituted for ethanol and the wash was repeated three times. The resulting solid was dried on a rotary evaporator to give 165mg of a white solid in 12% yield. ?H NMR (500 MHz, Deuterium Oxide) 8.61 (s, 2H), 5.07 (s, 1H), 4.21 (s, 1H), 3.17 – 3.02 (m, 2H), 1.92 – 1.74 (m, 2H), 1.49 (d, J = 6.4 Hz, 3H), 1.44 – 0.82 (m, 26H), 0.79 – 0.64 (m, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,287714-35-6, its application will become more common.

Reference:
Patent; SIGNUM BIOSCIENCES, INC.; VORONKOV, Michael; PEREZ, Edwardo; HEALY, Jason; FERNANDEZ, Jose; (139 pag.)WO2018/132759; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1005-38-5 , The common heterocyclic compound, 1005-38-5, name is 4-Amino-6-chloro-2-(methylthio)pyrimidine, molecular formula is C5H6ClN3S, 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 36 Using the method of Example 35, thiomorpholine was reacted with 4-amino-6-chloro-2-methylthiopyrimidine to provide 4-amino-2-methylthio-6-(4-thiomorpholino)pyrimidine as a yellow solid, m.p. 144-145 C. The structural assignment was supported by nuclear magnetic resonance spectral analysis.

The synthetic route of 1005-38-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Riker Laboratories, Inc.; US4503050; (1985); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 7627-39-6, 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. 7627-39-6, name is 2,4-Dichloro-5-(ethoxymethyl)pyrimidine. A new synthetic method of this compound is introduced below.

[0133] To a stirred solution of 3-hydroxy-10-(methyl-d3)-9,10,11,12-tetrahydro-8H- [1,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one-10,11,11-d3 (INT-1) (200.0 mg, 0.6 mmol) in DMSO (4 mL) was added K2CO3 (180.8 mg, 1.3 mmol) and stirred at room temperature for 40 mins followed by addition of 2,4-dichloro-5-(ethoxymethyl)pyrimidine (203.4 mg, 1.0 mmol). This reaction mixture was stirred at room temperature overnight. LCMS showed the reaction was complete. The reaction mixture was passed though silica gel and purified by reverse phase prep-HPLC to afford 3-((2-chloro-5-(ethoxymethyl)pyrimidin-4-yl)oxy)-10-(methyl-d3)- 9,10,11,12-tetrahydro-8H-[1,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one-10,11,11-d3 (I-2) (111.1 mg, 39.0%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta 9.36 (d, J = 9.0 Hz, 1H), 8.71 (s, 1H), 8.19 (s, J = 9.0 Hz, 1H), 8.12 (s, 1H), 7.86 (d, J = 9.0 Hz, 1H), 7.63 (d, J = 9.0 Hz, 1H), 4.66 (s, 1H), 3.62 (dd, J = 4.0 Hz, 2H), 1.20 (t, J = 4.0 Hz, 3H). MS m/z (M+H): 476.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7627-39-6, its application will become more common.

Reference:
Patent; CELGENE CAR LLC; MALONA, John; SURAPANENI, Sekhar S.; (116 pag.)WO2018/170201; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4983-28-2, 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 4983-28-2 as follows.

Compound 3-(dimethylamino)propan-1-ol (825.28 mg, 8 mmol) and triphenylphosphine (2.517 g, 9.6mmol) were added successively to a suspension of 19 (1.044 g, 8 mmol) in THF (15 mL) under nitrogen.A solution of DIAD (1.67 g, 9.6 mmol) in THF (2 mL) was then slowly added dropwise with ice cooling.The resultant solution was stirred at room temperature for 12 hours. The aqueous phase wasextracted with dichloromethane (40 mL 3). The combined organic layer was washed with H2O (40 mL)and brine (20 mL), and then dried over anhydrous Na2SO4, filtered and evaporated in vacuo. Theresidue was purified by flash chromatography over silica gel (DCM/MeOH = 40:110:1) to give 20a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4983-28-2, its application will become more common.

Reference:
Article; Zhang, Niu-niu; An, Bai-jiao; Zhou, Yan; Li, Xing-shu; Yan, Ming; Molecules; vol. 24; 6; (2019);,
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. 55084-66-7, name is 4-Chloro-2-(methylthio)pyrimidine-5-carbonyl chloride, 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. category: pyrimidines

To a mixture of 4-chloro-2-methylsulfanylpyrimidine-5-carbonyl chloride prepared above (113 mg, 0.54 mmol) in dichloromethane was added 4-fluoroaniline (56 muL, 0.59 mmol). This was followed by the dropwise addition of DIPEA. The mixture was stirred for 15 min, the mixture was diluted with dichloromethane, washed with water and saturated aqueous sodium bicarbonate and was dried over sodium sulfate. Filtration and concentration afforded a residue that was purified by trituration from ethyl acetate with hexanes. The resulting off-white solid (122 mg, 0.41 mmol, 76%) was sufficiently pure to use without further purification. 1H NMR (300 MHz, DMSO-d6) delta 10.7 (s, 1H), 8.86 (s, 1H), 7.69 (m, 2H), 7.23 (m, 2H), 2.56 (s, 3H); MS (EI) m/z 296.2 (M-H)-.

With the rapid development of chemical substances, we look forward to future research findings about 55084-66-7.

Reference:
Patent; UCB SA; US7176310; (2007); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia