Day: May 17, 2021

Related Products of 304693-66-1, 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.304693-66-1, name is 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde, molecular formula is C6H3F3N2O, molecular weight is 176.096, as common compound, the synthetic route is as follows.

To a magnetically stirred solution of methyl Grignard (19.9 mL of a 3 M solution in ether (Et2O), 59.7 mmol) in Et2O (167 mL) was added a solution of 2-trifluoromethylpyrimidine-5-carbaldehyde (9.56 g, 54.3 mmol) in Et2O (50 mL) at 0 C., and the resulting pale yellow solution was warmed to room temperature (RT) and stirred for 2.5 h. The reaction was quenched by the addition of saturated aqueous ammonium chloride (NH4Cl) (50 mL) at 0 C., and the mixture was warmed to RT. The phases were separated and the organic phase was dried over Na2SO4, filtered, and concentrated to give a light yellow oil (9.32 g crude). The oil was purified by flash chromatography (330 g SiO2, 0>100% EtOAc/hexanes gradient) to give 1-(2-trifluoromethylpyrimidin-5-yl)ethanol (E) (8.87 g, 85%) as a light yellow solid: mp 43-45 C.; 1H NMR (300 MHz, CDCl3) ? 8.92 (s, 2H), 5.15-5.07 (m, 1H), 2.26 (d, J=4.0 Hz, 1H), 1.62 (d, J=6.5 Hz, 3H); MS (EI) m/z 192 (M)+.

Statistics shows that 304693-66-1 is playing an increasingly important role. we look forward to future research findings about 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde.

Reference:
Patent; DOW AGROSCIENCES LLC; US2010/56534; (2010); 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. 425394-89-4, name is 4,6-Dichloropyrimidin-5-ol, the common compound, a new synthetic route is introduced below. HPLC of Formula: C4H2Cl2N2O

(1) 5-(Benzyloxy)-4,6-dichloropyrimidine, INT 45 To a solution of INT 37 (content 90%, 6.50 g, 35.50 mmol) in DMF (120 mL) was added benzyl bromide (8.42 mL, 70.90 mmol) followed by potassium carbonate (14.70 g, 106.36 mmol). The reaction mixture was stirred at 60 C. for 1 hr. The mixture was concentrated. The residue was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica; cyclohexane/EtOAc gradient, 0-10%) to afford INT 45 as a colorless oil. UPLC-MS: MS (ESI): [M+H]+ 255.1, rt=1.15 min. 1H NMR (DMSO-d6): delta (ppm) 8.72 (s, 1H), 7.57-7.50 (m, 2H), 7.48-7.37 (m, 3H), 5.19 (s, 2H).

The synthetic route of 425394-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ANGST, Daniela; GESSIER, Francois; VULPETTI, Anna; US2015/152068; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 151266-23-8, 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 151266-23-8 as follows.

Example 13. l-(4-(4-amino-l-cyclopentyl-lH-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)-3- (3-(trifluoromethyl)phenyl)urea (AD60); [0182] A synthetic strategy for Cmpd AD60 is depicted in Scheme 8 following. Scheme 8[0183] Reagent 3-iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine) (0.5g; 1.9 mmol; Apsel et al., 2008, Id.) was combined with cyclopentyl iodide (0.24 mL; 2.1 mmol), l .Og K2CO3, in 20 mL DMF and heated to 45 C under argon for 2 hours. The reaction was filtered to remove solid K2CO3, and the filtrate was combined with brine and the organic product was extracted in CH2Cl2 (3x 50 mL). The combined organic layer was concentrated in vacuo and purified by silica gel chromatography (MeOH/Chloroform; 5:95) to afford l-cyclopentyl-3- iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 330.0, calculated 330.0). 4-nitrophenyl boronic acid (190 mg, 1.1 mmol; Sigma-Aldrich), was coupled to 1- cyclopentyl-3-iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine (150mg, 0.456 mmol) via the Suzuki reaction in 6 mL 1,2 methoxy ethane, 1 mL of saturated sodium carbonate, 1.65 mL EtOH, and 200 mg of polymer-bound tetrakis palladium. The reaction was stirred under argon for 12 hours at room temperature, filtered through Whatman paper to remove palladium, mixed with brine, extracted in chloroform and the product was subsequently purified on silica in EtOAc and concentrated in vacuo. The purified solid l~cyclopentyl-3-(4- nitrophenyl)-lH-pyrazolo[3,4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 325.0, calculated 325.1 ; lOOmg, 0.31 mmol) was combined with Zinc dust (605 mg, 9.25 mmol), 10 mL THF, 0.35 mL HOAc for 12 hours at room temperature under Argon. The reaction was filtered through CeIi te, extracted with EtOAc and concentrated in vacuo to yield 3-(4- aminophenyl)-l -cyclopentyl- lH-pyrazolo [3, 4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 295.0, calculated 295.2). To this reduced product, molar equivalents of3-(trifluoromethyl)phenyl isocyanate (Sigma-Aldrich) were added dropwise in ice-cold CH2C12. The reaction proceeded until completion as judged by TLC, was concentrated in vacuo, resuspended in 50:50 H20-CH3CN, and purified on a Cl 8 column in CH3CN/H20/0.1%TFA (1-100% gradient) to yield AD60 l-(4-(4-amino-l -cyclopentyl- IH- pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea (ESI-MS m/z [M+H]+ found 482.2, calculated 482.0).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,151266-23-8, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; DAR, Arvin; SHOKAT, Kevan M.; WO2010/45542; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route 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.

Example 4; 4-Chloro-2-methylsulfinyl-8-(“4-trifluoromethyl-phenvD-8H- pyridor23-Patent; GLAXO GROUP LIMITED; WO2006/104917; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 75833-38-4, 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 75833-38-4, name is 2-Chloropyrimidine-4-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-chloropyrirnidine-4-carbonitrile (900 mg, 6.45 mmol) in dioxane (8 mL)/water (2 mL) was added K2C03 (2.20 g, 16.12 mmol), Pd(dppf)Cl2 (1.0 g, 1.29 mmol) and 4,4,5, 5-tetramethyl-2-vinyl-l,3,2-dioxaborolane (1.5 g, 9.67 mmol). The resulting mixture was stirred at 90 C overnight. After cooling to RT, the mixture was diluted with water (10 mL) and extracted with EtOAc (30 mL x 3). The combined organic layers were washed with brine, dried over Na2SC>4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography column (9% EtOAc in petroleum ether) to give the title compound as a solid. LRMS m/z (Mu+Eta) 132.1 found, 132.1 required.

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 75833-38-4, 2-Chloropyrimidine-4-carbonitrile.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel; LUO, Yunfu; (85 pag.)WO2016/100156; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1208901-69-2, Adding some certain compound to certain chemical reactions, such as: 1208901-69-2, name is 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride,molecular formula is C7H8Cl3N3, 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 1208901-69-2.

2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride (20.0 g, 83.2 mmol) prepared according to Reference Example 1 was dissolved in acetonitrile (200 mL), and the solution was mixed with dimethylaminopyridine (752 mg), di-tert-butyl dicarbonate (20.9 g) and triethylamine (11.6 mL), followed by stirring at room temperature for sixteen hours. After checking the completion of the reaction by thin layer chromatography, the reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The solution was sequentially washed with a 5% aqueous citric acid solution, water, a saturated aqueous sodium bicarbonate solution and brine, was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) and thereby yielded tert-butyl 2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-6-car boxylate (22.2 g, in a yield of 88%).

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. 1208901-69-2, 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1552842; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1233026-31-7, 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 1233026-31-7 as follows.

Step 2: Potassium carbonate (0.89 g, 6.45 mmol) was added at room temperature to an oven-dried, nitrogen cooled flask containing a suspension of ethylene glycol (1.3 mL, 23.4 mmol) in DMF (29 mL) and the mixture was then stirred for 15 minutes. 2-Chloro-4- (methylsulfonyl)pyrimidine (1.13 g, 5.86 mmol) was then added. The solution was stirred for 1.5 h at room temperature, then diluted with EtOAc (30 mL) and washed with 1 : 1 watenbrine (3 x 50 mL). The organic extracts were dried over sodium sulfate, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes) to afford 2-[(2-chloropyrimidin-4-yl)oxy]ethanol as a pale yellow solid. MS ESI calcd. for C6H8C1 202 [M + H]+ 175, found 175.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1233026-31-7, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michele, R.; ALTMAN, Michael, D.; ROMEO, Eric, T.; VITHARANA, Dilrukshi; CASH, Brandon; SIU, Tony; ZHOU, Hua; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; HAIDLE, Andrew, M.; CHILDERS, Kaleen Konrad; MADDESS, Matthew, L.; REUTERSHAN, Michael, H.; DUCHARME, Yves; GUERIN, David. J.; SPENCER, Kerrie; BEAULIEU, Christian; TRUONG, Vouy Linh; GUAY, Daniel; NORTHRUP, Alan, B.; TAOKA, Brandon, M.; LIM, Jongwon; FISCHER, Christian; BUTCHER, John, W.; OTTE, Ryan, D.; SUN, Binyuan; WO2013/192125; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 38696-21-8, 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. 38696-21-8, name is 5-Bromo-N,N-dimethylpyrimidin-2-amine, molecular formula is C6H8BrN3, 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 5-bromo-N,N-dimethylpyrimidin-2-amine (0.966 g, 4.78 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.46 g, 5.74 mmol), PdCl2dppf(DCM) (0.114 g, 0.14 mmol) and KOAc (1.407 g, 14.34 mmol) were placed under Ar in a 20 mL microwave flask. Anhydrous 1,2-dimethoxyethane (16 mL) was added and the flask was irradiated at 150 oC for 15 minutes. The reaction was filtered through celite, concentrated and slurried in EtOAc. The reaction was filtered through celite again and the organics were concentrated and purified by column chromatography 0 to 30 % EtOAC in Hexanes. The material was isolated as a light teal solid (0.718 g, 60 % yield). 1H NMR (400 MHz, CDCl3) delta 8.59 (s, 2H), 3.21 (s, 6H), 1.31 (s, 12H).13C NMR (100 MHz, CDCl3) delta 164.1, 83.7, 77.4, 37.2, 25.2, 24.9. HRMS (EI+) m/z calculated for C12H12BN3O2 [M+H]+: 250.1721, found: 250.17189.

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 38696-21-8, 5-Bromo-N,N-dimethylpyrimidin-2-amine.

Reference:
Patent; EMORY UNIVERSITY; SHI, Qi; KAISER, Thomas; DIRADDO, John; SNYDER, James P.; LIOTTA, Dennis C.; DENTMON, Zackery; (67 pag.)WO2017/197151; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 126352-69-0, 4,5,6,7-Tetrahydropyrazolo[1,5-a]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, Application In Synthesis of 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine

N-Iodosuccinimide (0.581 g, 2.58 mmol) was added to 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (0.265 g, 2.15 mmol) in acetonitrile (5 mL) at r.t. under nitrogen. The resulting solution was stirred at r.t. for 1 h before water (20 mL) was added. Stirring was continued for 1.5 h, and then the reaction mixture was extracted with MTBE (3×20 mL). The combined organic layers were washed sequentially with 2 M aqueous NaOH (20 mL), Na2S2O3 solution (20 mL, 10% w/v), and saturated aqueous sodium chloride (20 mL) before being dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford 3-iodo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (0.155 g, 28.9%) as a white crystalline solid. 1H NMR (400 MHz, CDCl3, 30 C.) 2.16 (2H, q), 3.32-3.44 (2H, m), 3.98 (1H, s), 4.12 (2H, t), 7.24 (1H, s). m/z: ES+[M+H]+ 250.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,126352-69-0, 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; Barlaam, Bernard; De Savi, Christopher; Hawkins, Janet; Hird, Alexander; Lamb, Michelle; Pike, Kurt; Vasbinder, Melissa; (134 pag.)US2016/376287; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7355-55-7, 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 7355-55-7, name is 2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one. This compound has unique chemical properties. The synthetic route is as follows.

2-Amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (1.5 g, 0.01 mol) at room temperatureIodine (5.1 g, 0.02 mol) was dissolved in ethanol/water (2:1, 100 mL) and heated to reflux for 2 h.The precipitate was cooled and precipitated, and the precipitate was filtered, washed with 1N sodium thiosulfate solution (2×30 mL) and water (2×50 mL).After drying, 2-amino-6-iodo-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one was obtained.

According to the analysis of related databases, 7355-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hebei Medical University; Wang Lei; Liu Yi; Zhang Congying; Gao Tianfeng; Zheng Qianqian; (37 pag.)CN110078735; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia