Pyrimidines

Reference of 1445-39-2, 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. 1445-39-2, name is 2-Amino-5-iodopyrimidine. A new synthetic method of this compound is introduced below.

A mixture of alkyne 7 (710 mg, 2.224 mmol), iodopyrimidine 4 (676 mg, 3.06 mmol), palladiumtetrakistriphenylphosphine (290 mg, 0.251 mmol) and copper (I) iodide (103 mg, 0.541 mmol) was suspended in degassed mixture of acetonitrile (15 mL) and triethylamine (5 mL, 35.9 mmol). The thick mixture was then stirred under argon at 82C for 3h; cooled down to room temperature and diluted with DCM, washed with saturated NH4C1, dried over MgSO4, filtered and concentrated. The purification was performed by flash column chromatography on silica gel (eluent EtOAc) to afford compound 8 (526 mg, 57% yield). IH NMR (400 MHz, DMSO-d6) delta (ppm): 8.97 (s, IH), 8.46-8.41 (m, 2H), 8.19 (s, IH), 7.79 (s, IH), 7.50 (d, J = 8.0 Hz, IH), 7.41 (t, J = 7.8 Hz, IH), 7.26 (t, J = 8.0 Hz, IH), 7.14 (s, 2H), 7.08-7.02 (m, 3H). MS (m/z): 413.1 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1445-39-2, 2-Amino-5-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; METHYLGENE INC.; WO2009/100536; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 104048-92-2, 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. 104048-92-2, name is 4-(Trifluoromethyl)pyrimidin-2(1H)-one, molecular formula is C5H3F3N2O, 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.

Example 259 Methyl-m-tolyl-carbamic Acid 4-trifluoromethyl-pyrimidin-2-yl Ester At 0 C. diphosgene (0.99 g, 5.00 mmol) was added to a stirred solution of 4-trifluoromethyl-2-hydroxypyrimidine (1.64 g, 10.0 mmol) in tetrahydrofuran (25 ml). The cooling bath was removed and stirring was continued at room temperature for 1 hour. Methyl-m-tolyl-amine (0.30 g, 2.50 mmol) was added to one-fourth of the solution. After stirring overnight at room temperature the solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (20:80)) followed by preparative HPLC, yielding the title compound (51 mg, 7%) as a colourless oil. 1H NMR (300 MHz, CDCl3): (2.37 (s, 3H), 3.42 (br.s, 3H), 7.07-7.31 (m, 4H), 7.52 (br.s, 1H), 8.92 (br.s, 1H); HPLC-MS (Method A): m/z=334 (M+Na); Rt=3.92 min.

According to the analysis of related databases, 104048-92-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ebdrup, Soren; de Jong, Johannes Cornelis; Jacobsen, Poul; Hansen, Holger Claus; Vedso, Per; US2003/166644; (2003); A1;,
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Pyrimidine – Wikipedia

Related Products of 134000-96-7 ,Some common heterocyclic compound, 134000-96-7, molecular formula is C5H4ClFN2, 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.

N-(5-Fluoro-4-methylpyrimidin-2-yl)-8-(4-methoxybenzyl)-6-(2-methoxyethyl)-4,5,6,8-tetrahydropyrazolo[3,4-b]thiazolo[4,5-d]azepin-2-amine According to Scheme 4, Step 2: A solution of 8-(4-methoxybenzyl)-6-(2-methoxyethyl)-4,5,6,8-tetrahydropyrazolo[3,4-b]thiazolo[4,5-d]azepin-2-amine (200 mg, 0.39 mmol), 2-chloro-5-fluoro-4-methylpyrimidine (93.0 mg, 0.63 mmol), Cs2CO3 (339 mg, 1.04 mmol), Xantphos (45 mg, 80 mumol) and Pd(OAc)2 (12 mg, 50 mumol) in dioxane (1.7 mL) was stirred at 120 C. for 30 min. The crude solution was cooled down and diluted with 10 mL of water and 10 mL of EtOAc. The aqueous layer was extracted twice with EtOAc. The combined organic layers dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel using DCM/MeOH (100:0 to 98:2) as eluent to afford the title compound (138 mg, 54%) as a beige solid. UPLC-MS (M1): RT=1.16 min; MS m/z ES+=496.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,134000-96-7, its application will become more common.

Reference:
Patent; Bolea, Christelle; Boudou, Cedric; Celanire, Sylvain; Darmency, Vincent; Mordant, Celine; Pericolle, Vincent; Regereau, Yannick; Rocher, Jean-Philippe; Souissi, Radouane; Tang, Lam; US2014/349994; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1337532-51-0, 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. 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below.

To a mixture of 1-(4-bromo-3-methylphenyl)-3-(3,5-difluorophenyl)pyrrolidin-2-one (0.6 g, 1.6 mmol, 1.0 equiv), bis(pinacolato)diboron (0.41 g, 1.6 mmol, 1.0 equiv), and potassium carbonate (0.48 g, 4.9 mmol, 3.0 equiv) was added 1 ,4-dioxane (10 ml_), and the mixture was degassed with Ar gas for 10 minutes. PdCI2 (dppf)-CH2Cl2 adduct (0.1 1 g, 0.08 mmol, 0.05 equiv) was added and degassed with Ar for 10 minutes. The reaction mixture was stirred for 3 h at 100 C in a sealed vessel. After consumption of SM, the reaction mixture was cooled to room temperature. 5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.37 g, 1.6 mmol, 1.0 equiv) and saturated aqueous NaHC03 (12 ml_) were added and degassed with argon for 10 min. PdCl2(dppf)-CH2Cl2 adduct (0.1 1 g, 0.08 mmol, 0.05 equiv) was added, the vessel was sealed, and the reaction mixture was stirred overnight at 100C. After consumption of SM, the reaction mixture was poured onto water and extracted with ethyl acetate (2 x 30 ml_). The combined organic layers were washed with brine solution (30 ml_), dried over Na2S04 and evaporated the solvent under reduced pressure to afford the crude product. The crude product was purified by flash column chromatography with 100 – 200 silica gel (24g column) and eluted with 3% MeOH in DCM mobile phase to afford the titled product 1-(4-(4-amino-7-methyl-7/-/-pyrrolo[2,3- d]pyrimidin-5-yl)-3-methylphenyl)-3-(3,5-difluorophenyl)pyrrolidin-2-one (0.1 g, 14%) as off white solid. LCMS (ES) m/z = 434.2 [M+H]+. H NMR (400 MHz, DMSO-d6) delta 2.21 – 2.27 (m, 4H), 2.54 – 2.61 (m, 1 H), 3.73 (s, 3 H), 3.93 – 4.07 (m, 3H), 5.54 (br, 2 H), 7.10 – 7.15 (m, 4 H), 7.25 (d, J=8.0 Hz, 1 H), 7.60 – 7.68 (m, 2 H), 8.13 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1337532-51-0, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 10320-42-0, 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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine, molecular formula is C4H2ClN3O2, 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.

A mixture of 1 ,4-diazabicyclo[3.2.2]nonane (0.87 g, 6.90 mmol), 2-chloro-5- nitro-pyrimidine (1.56 g, 6.27 mmol) and dioxane (75 ml) was stirred at room- temperature for 15 h. Aqueous sodium bicarbonate (20 ml, 10percent) was added followed by extraction with ethylacetate (3 x 20 ml). The organic phase was dried and evaporated and a yellow powder was isolated. Yield 0.86 g (55percent). Mp 135-139or V”y .

According to the analysis of related databases, 10320-42-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NeuroSearch A/S; WO2007/138039; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-65-8, 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.22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.

To a mixture of 2-chloro-5-methoxypyrimidine (1.5 g), 2-(2-fluoro-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan (2.5 g), a 2 M sodium carbonate aqueous solution (11 mL), and DME (10 mL) was added tetrakistriphenylphosphinepalladium(0) (500 mg) under nitrogen atmosphere. The resulting mixture was heated with stirring at 80¡ã C. for 3 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layers were washed with saturated brine, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Intermediate compound 1 represented by the following formula (2.0 g).

The chemical industry reduces the impact on the environment during synthesis 22536-65-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sumitomo Chemical Company, Limited; ORIMOTO, Kohei; NOKURA, Yoshihiko; NAKAJIMA, Yuji; TANABE, Takamasa; (52 pag.)US2018/317485; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6299-25-8, 4,6-Dichloro-2-(methylthio)pyrimidine, 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, 6299-25-8, blongs to pyrimidines compound. Application In Synthesis of 4,6-Dichloro-2-(methylthio)pyrimidine

(1) n-Butyl lithium(1.7M hexane solution, 295 mL) was added dropwise to a solution of diisopropylamine(47.7 g) in THF(1.4 L) at -78C under nitrogen atmosphere for 30 minutes and stirred for additional 30 minutes. A solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine(40.0 g) in THF(200 mL) was added dropwise to the reaction solution for an hour and stirred for an additional hour. The reaction solution was poured into dry ice(800 g) slowly and the mixture was stirred for 2 hours. Hydrochloric acid(1N) was added slowly, ethyl acetate was added thereto and the mixture was washed with water and brine. The aqueous layer was extracted with ethyl acetate, the combined organic layer was dried over magnesium sulfate and the solvent was distilled away. Hexane was added and the solid was triturated and dried to give 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid(45.51 g) as a pale brown solid. APCI-MS(m/e):237/239[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,6299-25-8, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP1970373; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 16357-69-0, 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. 16357-69-0, name is 4-Aminopyrimidine-5-carbonitrile, molecular formula is C5H4N4, 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.

4-Aminopyrimidine-5-carbonitrile (0.945 g, 7.87 mmol) was suspended in water (9.50 mL) and mixture was chilled briefly. Sulfuric acid (1.90 mL) was added. Solid went into solution, resulting in a clear yellow solution. Palladium on carbon (10%; 143 mg, 134 mumol) was added and solution was hydrogenated (RT; 18-30 psi) for 90 minutes. The mixture was filtered through a bed of Celite to remove the catalyst. The clear, pale yellow filtrate was treated with concentrated ammonium hydroxide to neutralize the acid. After chilling, the solid was collected, washed with cold water and air-dried with suction under house vacuum to give 4-amino-pyrimidine-5-carbaldehyde. (Yield 0.654 g, 5.31 mmol, 67.5%).

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 16357-69-0, 4-Aminopyrimidine-5-carbonitrile.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); 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 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Methyl 2,6-dichloropyrimidine-4-carboxylate

Methyl 2-chloro-6- [(36^-3 -methylmorpholin-4-yllpyrimidine-4-carboxylateMethyl 2,6-dichloropyrimidine-4-carboxylate (4.4 g, 21.25 mmol) in DCM (20 mL) was cooled in ice and treated dropwise with 3S-3-methylmorpholine (2.37g, 23.4 mmol) and DIPEA (8.15 mL, 46.8 mmol). After 3 hours polymer supported isocyanate scavenger resin (Ig) was added and the mixture was stirred for 30 minutes then filtered. The solution was evaporated and purified by flash silica chromatography, eluting with 5 – 20% methanol in DCM, to give the desired material as a white solid (5.0 g).NMR Spectrum: 1H NMR (300.132 MHz, DMSOd6) delta 1.23 (3H, d), 3.16 – 3.36 (2H, m), 3.45 (IH, td), 3.59 (IH, dd), 3.71 (IH, d), 3.87 (3H, s), 3.93 (IH, dd), 4.33 – 4.56 (IH, m), 7.28 (IH, s)LCMS Spectrum: MH+ 272.38, Retention Time 1.52 Method: Monitor Base

With the rapid development of chemical substances, we look forward to future research findings about 6299-85-0.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7751; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1004-17-7, 2-Methylpyrimidine-4-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, Quality Control of 2-Methylpyrimidine-4-carbaldehyde, blongs to pyrimidines compound. Quality Control of 2-Methylpyrimidine-4-carbaldehyde

4-Dimethoxymethyl-2-methyl-pyrimidine (4.5 g, 26.7 mmol) was added to a solution of HBr (48% in H2O, 10 niL) and stirred at room temperature for 2 hours. It was then diluted with water and washed with diethylether (2x). The aqueous layer was carefully neutralized with saturated sodium carbonate and extracted with ethyl acetate (2x). The combined extracts were dried over MgSO4. 2-Propanol (100 mL) was added. To this solution, aniline (2.5 mL, 26.7 mmol) was added and followed with diphenylphosphite (5.1 mL, 26.7 mmol). The reaction mixture was stirred at room temperature overnight and then concentrated. The residue was purified on silica gel column with 20% ethyl acetate/CH2Cl2 to give a yellow solid (3.3 g, 29% for 2 steps) as the desired product. MS (ESP+) m/z 432.2 (M + 1).

The synthetic route of 1004-17-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC; WO2006/26305; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia