Pyrimidines

Reference of 22536-66-9, 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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. A new synthetic method of this compound is introduced below.

To a solution of 0.07 g (0.19 mmol, 1.0 eq.) of(S)-1-amino-N-(3-chloro-4-fluorophenyl)-7- fluoro-2,3 -dihydro- 1H-indene-4-carboxami de hydrochloride (Vild) and 30 mg (0.21 mmol, 1.10 eq.) of 2-chloropyrimidine-4-carboxamide in 2 mL of NIVIP was added 0.07 ml (0.39mmol, 2.0 eq.) of N,N-diisopropylethylamine, and the mixture was subjected to microwave irradiation maintaining a reaction temperature of 130 C for 1 h. The mixture was diluted with 50 mL of ethyl acetate and washed 2 x 20 ml of water followed by 10 mL of brine. The organic phase was dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography (Si02, eluting with a linear gradient of 0-30%ethyl acetate/hexanes) to provide 24 mg (0.05 mmol, 29%) of(S)-2-((4-((3-chloro-4- fluorophenyl)carbamoyl)-7-fluoro-2,3 -dihydro- 1H-inden- 1 -yl)amino)pyrimidine-4- carboxamide (104). LCMS: m/z found 444. 1/446.1 [M+H]. HPLC: RT = 4.13 mm (Method A); ?H NIVIR (300 MFIz, Methanol-d4) 8.50 (d, 1H), 7.93 (dd, 1H), 7.61-7.72 (m, 1H), 7.50- 7.60 (m, 1H), 7.16-7.28 (m, 2H), 7.03 (t, 1H), 5.88-5.95 (m, 1H), 3.07-3.48 (m, 2H), 2.55-2.66(m, 1H),2.10(m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-66-9, its application will become more common.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); A1;,
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Electric Literature of 3740-92-9, 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.3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine, molecular formula is C10H6Cl2N2, molecular weight is 225.07, as common compound, the synthetic route is as follows.

EXAMPLE IX Seven grams of 4,6-dichloro-2-phenylpyrimidine is added in small portions to 30 ml. of beta-methoxyethylamine with slight warming and stirring. The resulting mixture is heated on a steam bath for several minutes and then poured into 500 ml. of water. The product thus obtained (5.1 g.) is recrystallized from n-heptane to afford 4-chloro-6-(2-methoxyethylamino)-2-phenylpyrimidine, 48.5°-50°C. Anal. for C13 H14 N3 OCl: Calcd. C, 59.21; H, 5.35; N, 15.93. Found: C, 59.32; H, 5.31; N, 15.72.

Statistics shows that 3740-92-9 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloro-2-phenylpyrimidine.

Reference:
Patent; American Home Products Corporation; US3940395; (1976); A;,
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Electric Literature of 6299-85-0 , The common heterocyclic compound, 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, 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 a solution of Compound 8 (1.04 g, 5.0 mmol) and DIPEA (1.04 mL) in THF (5 mL) at 0 C. was added Compound 132 (0.92 g, 5.5 mmol). The mixture was warmed to RT and stirred overnight. The mixture was concentrated, diluted with water and extracted with EtOAc. The organic extracts were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SiO2, 0-80% EtOAc/DCM) to give Compound 133 as a white solid (1.5 g). Yield 89%. LC/MS: m/z=338 [M+H]+ (Calc: 337).

The synthetic route of 6299-85-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Purdue Pharma L.P.; Lynch, Stephen M.; Yao, Jiangchao; Park, Jae Hyun; Tafesse, Laykea; US2015/284383; (2015); A1;,
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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. 14160-93-1, name is 4-Amino-6-chloropyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below., Formula: C5H4ClN3O

Compound 1.2 (249 mg, 1.58 mmol, 1 eq.) and 2,4,6- trimethoxybenzylamine (free-based by saturated sodium bicarbonate wash) (313 mg, 1.59 mmol, 1 eq.) were dissolved in dichloromethane (3 mL) at room temperature. Acetic acid (91 muL, 1.58 mmol, 1 eq.) was added and the reaction mixture was heated in a microwave at 100C for 5 minutes. Sodium triacetoxyborohydride (410 mg, 1.94 mmol, 1.2 eq.) was added at room temperature and the reaction was stirred overnight. Saturated sodium bicarbonate solution and ethyl acetate were added to the reaction mixture and the layers were separated. The product was extracted twice more with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate solution, brine, and then dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the crude product was purified using silica gel column chromatography with a gradient of hexanes / ethyl acetate (l:l-M:2-»l:4-»0:100) followed by ethyl acetate / methanol (50:1) to afford compound 53.1 (287 mg, 0.846 mmol, 54%).

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, 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde.

Reference:
Patent; SUNESIS PHARMACEUTICALS, INC.; WO2006/65703; (2006); A1;,
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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. 36847-10-6, name is 4,6-Dibromopyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C4H2Br2N2

Synthesis Example 1 (0304) In this example, a method of synthesizing 9,9?-[pyrimidine-4,6-diyl bis(biphenyl-3,3?-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm) (the structural formula (100)), which is a heterocyclic compound of one embodiment of the present invention, is described. The structure of 4,6mCzBP2Pm is shown below. Synthesis of 4,6mCzBP2Pm (0305) First, 0.54 g (2.3 mmol) of 2,4-dibromopyrimidine, 1.8 g (5.0 mmol) of 3-(3-(9H-carbazol-9-yl)phenyl)phenyl boronic acid, and 69 mg (0.23 mmol) of tris(2-methylphenyl)phosphine were put into a 50-mL three-neck flask, and the air in the flask was replaced with nitrogen. (0306) Then, 4.9 mL of a 2M potassium carbonate aqueous solution, 12 mL of toluene, and 4 mL of ethanol were added to this mixture, and the mixture was degassed by being stirred under reduced pressure. To this mixture, 10 mg (0.045 mmol) of palladium(II) acetate was added and stirring was performed under a nitrogen stream at 90 C. for 16 hours. After the stirring, water was added to the mixture, and an aqueous layer was subjected to extraction with toluene. (0307) The obtained solution of the extract and an organic layer were combined, and the mixture was washed with water and saturated brine. Then, the mixture was dried with magnesium sulfate. This mixture was separated by gravity filtration, and the filtrate was concentrated to give an oily substance. The oily substance was purified by silica gel column chromatography (as the developing solvent, first hexane and toluene in a ratio of 5:1 were used, and then chloroform and ethyl acetate in a ratio of 50:1 were used). The obtained fraction was concentrated to give an oily substance. Chloroform was added to this oily substance, the mixture was suction-filtered through Celite and alumina, and the filtrate was concentrated to give an oily substance. This oily substance was purified by high performance liquid column chromatography (HPLC) (developing solvent: chloroform). (0308) The obtained fraction was concentrated to give an oily substance. This oily substance was recrystallized with toluene/hexane to give 1.0 g of a target white solid in a yield of 63%. (0309) By a train sublimation method, 0.99 g of the obtained white solid was purified. In the purification by sublimation, the white solid was heated at 320 C. under the conditions where the pressure was 2.7 Pa and the argon flow rate was 5 mL/min. After the purification by sublimation, 0.91 g of a pale yellow solid was obtained at a collection rate of 92%. A synthesis scheme of the above synthesis method is shown in (A-1) below. (0310) Analysis results by nuclear magnetic resonance (1H-NMR) spectroscopy of the pale yellow solid obtained by the above-described synthesis method are described below. FIGS. 15A and 15B show the 1H-NMR chart. FIG. 15B is a chart where the range from 7 (ppm) to 10 (ppm) on the horizontal axis (delta) in FIG. 15A is enlarged. The results revealed that 4,6mCzBP2Pm (the structural formula (100)), which is a heterocyclic compound of one embodiment of the present invention, was obtained in this example. (0311) 1H-NMR (CDCl3, 300 MHz): g=7.30 (td, J=7.2 Hz, 1.2 Hz, 4H), 7.39-7.50 (in, 8H), 7.59-7.66 (m, 4H), 7.72 (t, J=7.8 Hz, 2H), 7.78-7.83 (m, 4H), 7.89 (s, 2H), 8.13-8.20 (in, 7H), 8.45 (s, 2H), 9.34 (sd, J=1.2 Hz, 1H).

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, 36847-10-6, 4,6-Dibromopyrimidine.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; SEO, Satoshi; KUBOTA, Yuko; TAKAHASHI, Tatsuyoshi; MITSUMORI, Satomi; (77 pag.)US2016/308139; (2016); A1;,
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Reference of 160199-05-3, 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. 160199-05-3, name is 2,4-Dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, molecular formula is C10H4Cl2N2S, 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.

In a round bottom flask, intermediate 1-3 (10 g, 39.2 mmol), (9-phenyl-9H-indazol-2-yl)boronic acid (11.3 g,39.2 mmol), tetrakistriphenylphosphonium (1.4 g, 1.2 mmol), sodium hydroxide (3.9 g, 98 mmol) and tetrahydrofuran (200 mL)Mixed solvent with deionized water (100 mL). The reaction system was heated to reflux at 80 C. After the reaction is completed, it is cooled to room temperature.The reaction solution was diluted with distilled water. The reaction mixture was then extracted with dichloromethane and water.Purification by silica gel chromatography, recrystallization to give intermediate 1-6 (13.6 g, 78%)

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 160199-05-3, 2,4-Dichlorobenzo[4,5]thieno[3,2-d]pyrimidine.

Reference:
Patent; Zhejiang Huaxian Optoelectric Technology Co., Ltd.; Zheng Xianzhe; Huang Dong; Hua Wanming; Quan Meizi; Zhao Xiaoyu; (34 pag.)CN109678876; (2019); A;,
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Synthetic Route of 7504-94-1 , The common heterocyclic compound, 7504-94-1, name is 2-Hydrazinylpyrimidine, molecular formula is C4H6N4, 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.

A mixture of 2-hydrazinopyrimidine (100 mg, 0.91 mmol) and CDI (295 mg, 1.82 mmol) in THF (2 mL) was stirred at room temperature for 18 h. The solid material was removed by filtration, washing with ethyl acetate. The solid residue was purified by Biotage Isolera chromatography (silica gel, eluting with 0-20% MeOH in DCM) to give 20 mg (16% yield) of the title compound as a yellow solid.1H NMR (250 MHz, DMSO-d6) d 12.59 (s, 1H), 8.50 (dd, J = 2.0, 3.8 Hz, 1H), 8.28 (dd, J = 2.0, 7.0 Hz, 1H), 6.66 (dd, J = 3.8, 7.0 Hz, 1H). LCMS (Analytical Method E) Rt= 0.30 min, MS (ESIpos): m/z= 137.1 [M+H]+.

The synthetic route of 7504-94-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLACKTHORN THERAPEUTICS, INC.; JONES, Robert M.; BRANDT, Gary; (506 pag.)WO2020/97609; (2020); A1;,
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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.

A suspension of 4-((4-((benzo[d][1,3]oxathiol-6-yl)-2-fluorophenoxy)methyl)piperidine (155 mg, 0.45 mmol)), 2-chloro-5-methoxypyrimidine (78 mg, 0.54 mmol) and diisopropylethylamine (87 mg, 0.68 mmol) in acetonitrile (10 mL) was stirred at reflux overnight. Upon cooling, the reaction mixture was allowed to cool to ambient temperature and the solvent was removed in vacuo and the crude product was purified by column chromatography eluting with hexanes: ethyl acetate (4: 1) to obtain the title product (63 mg, 31%) as a white powder.

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; Peu Lama Na Perm Syutikeolseu In Keu .; Man Su-reu-ta-rek-su-ha-il; Cha Pi-beu-mi-ka-il; Yu Din-mi-ka-il; Ge Jen-cheu-be-i-yu-ri; Ni Ki-tin-al-rek-san-deu-reu; (190 pag.)KR2019/15535; (2019); A;,
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Reference of 1558-17-4, 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 1558-17-4 as follows.

General procedure: Irradiation procedure. The dimethylpyrazine or dimethylpyrimidine was placed in a Pyrex tube, attached to the vacuum line, and subjected to three freeze-thaw cycles. The remaining material was then allowed to vaporize into a quartz reaction flask (3 L) that had been evacuated overnight. The resulting pressure in the reaction flask ranged from 1.0 to 1.5 Torr. The flask was irradiated for 5 min. in a Rayonet reaction equipped with either 2, 4,6, 8, or 10 low-pressure 2537 A Hg lamps.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1558-17-4, its application will become more common.

Reference:
Article; Pavlik, James W.; Vongakorn, Tharinee; Kebede, Naod; Arkivoc; vol. 2017; 5; (2017); p. 216 – 228;,
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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. 1374639-77-6, name is (2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol, the common compound, a new synthetic route is introduced below. Safety of (2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol

A dry, nitrogen-flushed ACE-100L Reaction vessel is charged with 97.3 g of sodium cyanide, 2,500 g of (2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-c]pyrimidin-6-yl)methanol, A1c, 16,680 g (19.5 L) of dimethylamine, A1a (2.0M solution in THF), and 28,320 g (30.0 L) of anhydrous N,N-dimethylformamide. The mixture is stirred at 20±3 C. for 15 min. 2.06 kg of manganese(IV) oxide is then added. The dark slurry is stirred for 30 min and 12.36 Kg of manganese (IV) oxide is added in three portions (1st portion: 2.06 kg; 2nd portion: 4.12 g, and 3rd portion: 6.18 kg) every 30 min. After the last portion has been added, the sample is held for 1 h and then 6.18 kg of manganese(IV) oxide is added. The sample is held for 1 h. The reaction mixture is then sampled. The reaction is considered complete if the starting material, A1c is ?1.0±0.5% as determined by HPLC analysis. The reaction mixture is then filtered through a pad of celite to remove manganese (IV) oxide. The reactor and cake are rinsed with 23 L of ethyl acetate. The filtrate and distil are combined under reduced pressure (45±3 C., 20 mbar) to remove THF, dimethylamine and ethyl acetate. The sample is further distilled under reduced pressure (70±5 C., 5 mbar) to remove DMF. The concentrate is diluted with 35 L of ethyl acetate. The resulting dark solution is washed with aqueous ferrous sulfate solution (1 kg of FeSO4.7H2O in 14 L of water), 15 L of water and finally 15 L of 10% aqueous NaCl solution. The phases are separated after each wash. The organic phase is distilled (45 C., 50 mbar) to azeotropically remove water. The resulting crude A1 (2,788 g of a dark, thick, semi-solid residue) can be used directly in the next step.; 10 g of crude A1 and 9 mL of 1-propanol are warmed gently until a homogeneous, dark solution is obtained. The solution is cooled to 25+/-3 C. and 30 to 40 mL of hexane is slowly added. The sample is seeded and stirred until crystals are observed. An additional 50 to 60 mL of hexane is slowly added. The total volume of hexane added is about 90 mL. The slurry is held at 22+/-3 C. for 2 h, then cooled to 4 C. and held for an additional 2 h. The solids are filtered. The flask and filter cake are washed with hexane as needed. The filter cake is dried at 50 C., 50 mbar to afford 6.35 g of purified A1 as a light tan, crystalline solid. Recovery: 63.5%.Method 2:A solution of 10 g of crude A1 in 10 mL of EtOAc is prepared and loaded onto a 100 g bed of silica gel. The column is eluded with 300 mL of EtOAc/hexane (2/8) and the eluant is disgarded. The column is then elude with 800 mL of EtOAc/hexane (5/5) and the eluant is collected (No.2) for isolation of the product. The eluant (No.2) is concentrated to thin oil. 100 mL of hexane is slowly added and the sample is stirred at 22+/-3 C. for 2 h. The sample is cooled to 4 C. and held an additional 2 h. The solids are filtered. The flask and filter cake are washed with hexane as needed. The filter cake is dried at 50 C., 50 mbar to afford 6.05 g of purified A1 as a light tan, crystalline solid. Recovery 60.5%.

The synthetic route of 1374639-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Calienni, John Vincent; Chen, Guang-Pei; Gong, Baoqing; Kapa, Prasad Koteswara; Saxena, Vishal; US2012/115878; (2012); A1;,
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