Pyrimidines

Related Products of 50270-27-4 ,Some common heterocyclic compound, 50270-27-4, molecular formula is C5HCl3N2O, 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 2,4,6-trichloropyrimidine-5-carbaldehyde (2 g, 9.46 mmol) in EtOH (25 mL) at -78 °C under argon were added tert-butylhydrazine hydrochloride (1.18 g, 9.46 mmol) and TEA (6 mL, 42.57 mmol) dropwise. The mixture was stirred at -78 °C for 2 h, then at 0 °C for 3 h. The mixture was then concentrated under reduced pressure onto Celite and purified by silica gel chromatography eluting with 0- 1percent) MeOH in DCM to afford l-tert-butyl-4,6-dichloro-lH-pyrazolo[3,4-d]pyrimidine (1.7 g, 73percent) as an oil that solidified upon standing. LCMS (ESI) m/z 245 (M + H)+.

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. 50270-27-4, 2,4,6-Trichloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; WO2012/30924; (2012); 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. 939979-43-8, name is 5,7-Dichloro-3-methylpyrazolo[1,5-a]pyrimidine, the common compound, a new synthetic route is introduced below. COA of Formula: C7H5Cl2N3

5,7-Dichloro-3-methyl-pyrazolo[l,5-a]pyrimidine (190 mg, 938.52 mupiiotaomicron, 1 eq), (5-fluoro-3- pyridyl)boronic acid (138.86 mg, 985.45 muiotaetaomicron, 1.05 eq), Pd(dppf)Cl2 (68.67 mg, 93.85 muiotaetaomicron, 0.1 eq) and Cs2C03 (611.58 mg, 1.88 mmol, 2 eq) were taken up into a microwave tube in 1,4-dioxane (3 mL) and H20 (1 mL). The sealed tube was heated at 110 C for 1 h under microwave. The mixture was concentrated and water (10 mL) was added. The mixture was extracted with EtOAc (20 mL x 3). The combined organic layers were dried over Na2S04, filtered and concentrated to yield a residue which was purified on silica gel column chromatography (from PE/EtOAc = 1/0 to 10/3, TLC: PE/EtOAc = 3/1, Rf = 0.50) to yield 5-chloro-7-(5-fluoro-3-pyridyl)-3-methyl- pyrazolo[l,5-a]pyrimidine (130 mg, 494.92 mupiiotaomicron, 52.7% yield, 100.0%) purity) as a yellow solid. NMR (400 MHz, CDC13) delta ppm 8.97 (s, 1H), 8.69 (d, J = 2.7 Hz, 1H), 8.38-8.31 (m, 1H), 8.04 (s, 1H), 6.92 (s, 1H), 2.40 (s, 3H); ES-LCMS m/z 263.0, 265.0 [M+H]+.

The synthetic route of 939979-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYN THERAPEUTICS; CASTRO, Alfredo C.; EVANS, Catherine Anne; (632 pag.)WO2018/195397; (2018); A2;,
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Pyrimidine – Wikipedia

Application of 2927-71-1, 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.2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, molecular weight is 166.9685, as common compound, the synthetic route is as follows.

A solution of HOAc (2.4 g, 0.04 mol) in THF (15 mL) was added drop wise to a refluxing mixture of dichloro-5-fluoro-pyrimidine (3.34 g, 0.02 mol) and Zn (7.8 g, 0.02 mol) in THF (40 mL) over a 1-hour period. The mixture was refluxed for another 9 h. After cooling to room temperature, the solution was filtered to remove an insoluble solid. The solution containing 2-chloro-5-fluoro-pyrimidine was used directly in the next step reaction.

Statistics shows that 2927-71-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; Kalypsys, Inc.; US2005/234046; (2005); A1;,
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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. 591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, 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. Formula: C4H5N3

Pyrimidin-5-amine (9.84 mg, 0.104 mmol) was dissolved in DCM (1.0 mL) along with pyridine (0.039 mL, 0.487 mmol) and DIEA (0.032 mL, 0.183 mmol). Intermediate14SF (28 mg, 0.061 mmol) in 2 mL of DCM was added dropwise, and the reactionmixture was stirred at room temperature for 50 minutes. The reaction was quenched with1.0 N HC1 (0.5 mL). All solvent was removed under vacuum. The crude material wasdissolved in DMSO/THF (2:1, 6 mL) and purified via preparative LC/MS (method C,45-70% B over 30 mm, then a 5-mm hold at 100% B). Fractions containing the desiredproduct were combined and dried via centrifugal evaporation to yield Example 185 (1.6 mg, 4.3% yield). ?H NMR (500MHz, DMSO-d6) 8.86 (m, 3H), 8.76 (s, 1H), 8.60 (s, 1H), 7.90 (d, J=1 1.0 Hz, 1H), 7.85 (br. s., 1H), 5.45 (d, J7.9 Hz, 1H), 4.57 (d, J12.2 Hz, 1H), 4.45 (dd, J=12.2, 6.7 Hz, 1H), 4.09 (s, 3H), 3.68 (dd, J15.9, 9.8 Hz, 1H), 3.33 (d, J12.2 Hz, 1H), 2.64 (s, 3H); LC-MS: method C, 2 to 98% B. RT = 2.14 mm, MS(ESI) m/z: 519.30 (M+H) Analytical HPLC purity (method B): > 86%.

With the rapid development of chemical substances, we look forward to future research findings about 591-55-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); A1;,
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Application of 2915-16-4, 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 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

After introducing compound 5-1 (10 g, 22.7 mmol), 2-chloro-4,6-diphenylpyrimidine (CAS: 2915-16-4, 5.5 g, 20.6 mmol), tetrakis(triphenylphosphine)palladium (1.2 g, 1.0 mmol), potassium carbonate (7.1 g, 56 mmol), toluene (90 mL), ethanol (30 mL), and distilled water (30 mL) into a reaction vessel, the mixture was stirred for 4 hours at 120C. After completing the reaction, the mixture was added dropwise to methanol, and the obtained solid was filtered. The obtained solid was purified by column chromatography and recrystallization to obtain compound C-87 (5.5 g, 51 %).

According to the analysis of related databases, 2915-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; AHN, Hee-Choon; (41 pag.)WO2017/30283; (2017); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, 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, 16019-33-3, blongs to pyrimidines compound. name: 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

Step K.1 : Benzoic acid c s-3-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutylmethyl ester A mixture of (4,6-dichloro-pyrimidin-5-yl)-acetaldehyde (Astatech, 1.40 g, 7.31 mmol), benzoic acid 3-amino-cyclobutylmethyl ester (prepared as described in Org. Process Res. Dev. 2007, 11, 825-835., 1.5 g, 7.31 mmol), diisopropylethylamine (0.95 g, 7.31 mmol) and etha- nol (15 ml) were heated at reflux for 5.5 hours under an argon atmosphere. The reaction mix- ture was evaporated, taken up in THF (10 ml), aqueous HCI (4 ml, 4M) added and stood at room temperature for 1 hour. The volume of the mixture was then reduced under vacuum, made neutral with aqueous sodium bicarbonate solution, extracted 3X with DCM, the organic layers dried over sodium sulphate and evaporated. Purification by flash column chromatography, eluting with a DCM / EtOAc gradient gave the title compound. HPLC/MS tR 1.52 min, M+H 342.1 (Method X).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16019-33-3, its application will become more common.

Reference:
Patent; NOVARTIS AG; IRM LLC, a Delaware Limited Liability Company; CHEN, Bei; FAIRHURST, Robin, Alec; FLOERSHEIMER, Andreas; FURET, Pascal; JIANG, Songchun; LU, Wenshuo; MARSILJE, Thomas, H.; VAUPEL, Andrea; WO2011/64211; (2011); A1;,
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Pyrimidine – Wikipedia

Application of 22276-99-9, 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. 22276-99-9, name is 4-Amino-5-bromo-1H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H5BrN4, 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.

(S)-(4-Oxo-3-(1 -phenylethyl)-3,4-dihydropyrrolo[2, 1 -f][1 ,2,4]triazin-2-yl)methyl methanesulfonate (295 mg, 0.67 mmol) was dissolved in 5 ml_ dimethylformamide. 5- Bromo-7/-/-pyrrolo[2,3-d]pyrimidin-4-amine (156 mg, 0.73 mmol) and potassium carbonate (184 mg, 1.33 mmol) were added. The mixture was stirred at room temperature overnight. The crude was poured over water and the precipitate was filtered and washed with water to give the title compound (239 mg, 55%) as a white solid. Purity 70%

According to the analysis of related databases, 22276-99-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; GRACIA FERRER, Jordi; CARRASCAL RIERA, Marta; ERRA SOLA, Montserrat; WO2014/60431; (2014); A1;,
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Pyrimidine – Wikipedia

Related Products of 3435-29-8, 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. 3435-29-8, name is 4-Amino-6-phenylpyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 6-phenylpyrimidin-4-amine (170mg, 0.993mmol) in pyridine (3mL) was added 4-nitrobenzene-l-sulfonyl chloride (440mg, 1.99mol). The mixture was stirred at RT for two hours. The solvent was removed under reduced pressure to give a solid. The solid was purified by column chromatography to give 4-nitro-N-(6- phenylpyrimidin-4-yl)benzenesulfonamide (240mg, 68%). MS (ESI) m/z 354 [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,3435-29-8, its application will become more common.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; SHARPE, Arlene, H.; BUTTE, Manish, J.; OYAMA, Shinji; WO2011/82400; (2011); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 51674-77-2 ,Some common heterocyclic compound, 51674-77-2, molecular formula is C7H4ClN3, 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.

(S)-(-)-tert-Butyl 3-aminopyrrolidine-l-carboxylate (500 mg, 2.68 mmol), DCM(30 mL), DIPEA (2 mL) and cyclopropanecarbonyl chloride (0.28 mL, 3.0 mmol) were combined at r.t. and stirred for 2 days. The reaction was diluted with DCM (100 mL), washed with water, dried (MgS04) and evaporated in vacuo to give a brown oil (866 mg). The crude product was combined with MeOH (10 mL) and 2M HCl in Et20 (5 mL) and stirred at r.t. for 3 days. The reaction mixture was then evaporated in vacuo to give a brown gum (746 mg). The crude compound, Intermediate 9 (500 mg, 1.48 mmol), n- butanol (16 mL) and DIPEA (2 mL) were combined in a sealed tube and heated to 130C for 15 days. The reaction mixture was evaporated onto silica and purified by flash chromatography on silica, eluting with 0-100% EtOAc in isohexane, to give a tan solid (779 mg). The product was combined with MeOH (10 mL) and 2N HCl in Et20 (7 mL) and stirred at r.t for 19 h. The reaction mixture was then evaporated in vacuo to give a brown glass (689 mg). The resulting amine intermediate (HCl salt, 50 mg) was combined with 4-chloropyrido[3,2-d]pyrimidine (50 mg) in «-butanol (5 mL) and DIPEA (1 mL). The reaction mixture was heated in a sealed tube under microwave irradiation to 160C for 2 h. The mixture was evaporated to dryness and purified by preparative HPLC to give the title compound (32 mg) as a brown glass. deltaEta (DMSO-d6) 8.94-8.90 (2H, m), 8.52 (1H, s), 8.42 (1H, d, J6.4 Hz), 8.28-8.22 (1H, m), 8.17 (1H, dd, J 8.5, 1.6 Hz), 7.91 (1H, dd, J 8.5, 4.2 Hz), 7.56 (1H, dd, J 8.8, 6.4 Hz), 7.08 (1H, t, J 9.1 Hz), 6.00 (1H, t, J 7.2 Hz), 4.47-4.39 (1H, m), 4.02 (1H, dd, J 10.4, 6.8 Hz), 3.97-3.86 (2H, m), 3.70 (1H, dd, J 10.4, 6.9 Hz), 2.50 (3H, d, J2.2 Hz), 2.32-2.22 (1H, m), 2.00-1.91 (1H, m), 1.65-1.55 (4H, m), 0.75-0.66 (4H, m). LCMS (ES+) 486 (M+H)+, RT 8.15 minutes (Method 3).

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. 51674-77-2, 4-Chloropyrido[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2011/58108; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 10320-42-0, 2-Chloro-5-nitropyrimidine, 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: C4H2ClN3O2, blongs to pyrimidines compound. Formula: C4H2ClN3O2

A mixture of the pyrimidine compound (0.3 g, 2 mmol), Fe powder (560 mg, 10 mmol), NH4Cl (1.07 g, 20 mmol), EtOH (8 mL) and water (2 mL) was refluxed under N2 overnight. The mixture was cooled to RT and filtered. The filtrate was concentrated and dissolved in water. The mixture was basified with Na2CO3 and extracted with CH2Cl2 two times. The combined organic phases were dried over Na2SO4 and filtered. The filtrate was concentrated to yield the product (120 mg). MS (ESI) m/e (M+H+): 130. 1H NMR (DMSO) delta: 7.99 (s, 2H), 5.73 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10320-42-0, 2-Chloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Merck Sharp & Dohme Corp.; Coburn, Craig A.; Ludmerer, Steven W.; Liu, Kun; Wu, Hao; Soll, Richard; Zhong, Bin; Zhu, Jian; (155 pag.)US2019/127365; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia