Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, 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, SDS of cas: 26032-72-4, blongs to pyrimidines compound. SDS of cas: 26032-72-4

In the synthesis of intermediate 2,Using Intermediate 8 instead of Intermediate 1,Intermediate 10 was used instead of phenylboronic acid,The synthesis was carried out in the same manner. Under an argon gas flow,Intermediate 1 (11.9 g, 50 mmol) was added successively to the reaction vessel,Phenylboronic acid (7.9 g, 65 mmol),Tetrakis (triphenylphosphine) palladium (1.73 g, 1.5 mmol),Toluene 170 mL,Ethanol 30 mL,2M aqueous sodium carbonate solution (50 mL),And the mixture was heated under reflux for 8 hours.After the reaction solution was cooled to room temperature,The organic layer was separated,The organic solvent was removed by distillation under reduced pressure.The resulting residue was purified by silica gel chromatography,To give intermediate 2 (11.6 g, 49 mmol (yield 98%)).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; Mizuki, Yumiko; Ito, Hirokatsu; Haketa, Tasuku; Hayama, Tomoharu; Nishimura, Kazuki; Kawamura, Masahiro; Shibata, Mitsuru; (73 pag.)CN105408310; (2016); A;,
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Application of 62802-42-0, 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.62802-42-0, name is 2-Chloro-5-fluoropyrimidine, molecular formula is C4H2ClFN2, molecular weight is 132.5235, as common compound, the synthetic route is as follows.

Preparation 115 N-[(4aR,7aS)-6-(5-Fluoropyrimidin-2-yl)-7a-phenyl-4,4-a,5,7-tetrahydropyrrolo[3,4d][1,3]thiazin-2-yl]benzamide A solution of N-[(4aR,7aS)-7a-phenyl-4-a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (250 mg, 0.629 mmol), 5-fluoro-2-chloropyrimidine (167 mg, 1.26 mmol), 1,4-dioxane (10 mL), and triethylamine (318 mg, 3.14 mmol) is stirred at 110 C. for 4 hours. The reaction is cooled, diluted with water and extracted with dichloromethane. The organic layers are combined, dried, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1) to give the title compound (0.217 g, 80%). ES/MS (m/e): 434 (M+H).

The chemical industry reduces the impact on the environment during synthesis 62802-42-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eli Lilly and Company; BECK, James Peter; GREEN, Steven James; LOPEZ, Jose Eduardo; MATHES, Brian Michael; MERGOTT, Dustin James; PORTER, Warren Jaye; RANKOVIC, Zoran; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR, Leonard Larry; US2013/261111; (2013); A1;,
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Reference of 62802-38-4, 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.62802-38-4, name is 5-Bromo-2-fluoropyrimidine, molecular formula is C4H2BrFN2, molecular weight is 176.9745, as common compound, the synthetic route is as follows.

Step 3: A mixture of 1,3-dimethyl-1H-pyrazol-4-amine (453 mg, 4.66 mmol), 5- bromo-2-fluoropyrimidine (750 mg, 4.24 mmol) and DWA (1.62 mL, 21.8 mmol) in DM50 (5 mE) was heated with at 120 C for 2 h. The resulting mixture was cooled to it and quenched with water. The yellow solid was collected via filtration, washed with water, and dried in vacuum oven to give 5-bromo-N-(1,3-dimethyl-1H-pyrazol-4-yl)pyrimidin-2-amine (1.08 g, 99%). LC-MS (ESI) m/z 268, 270 (M+Hjb.

The chemical industry reduces the impact on the environment during synthesis 62802-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PLEXXIKON INC.; HOLLADAY, Mark W.; LIU, Gang; (267 pag.)WO2017/19804; (2017); A2;,
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Reference of 1193-21-1, 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 1193-21-1 as follows.

EXAMPLE 8 This example illustrates the preparation of (E)-methyl 2-[2-(4-fluoropyrimidin-6-yloxy)phenyl]-3-methoxypropenoate, an intermediate for the synthesis of compounds of the invention. A mixture of 4,6-dichloropyrimidine (6.50 g), sulphur tetrafluoride (20.8 g) and Arcton 113 (35 ml) was heated at 50 C. with stirring in a 100 ml Monel reactor for 3.3 hours. The temperature was increased to 100 C. over 25 minutes and maintained at 100 C. for a further 3 hours. The temperature was increased to 151 C. over 20 minutes and maintained at 151 C. for 3 hours. The vessel was then allowed to cool to room temperature. The reaction mixture was poured into saturated sodium hydrogen carbonate solution and extracted with dichloromethane. A sticky solid was observed at the interface and was removed by filtration. The layers were then separated. The organic layer was washed with water, and then distilled at atmospheric pressure to remove the dichloromethane. 4,6-Difluoropyrimidine was isolated by distillation in vacuo (50 C./100 mmHg) as a light yellow oil (400 mg; 7.3% yield); 1 H NMR delta: 6.61 (1H, s); and 8.69 (1H, s)ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-21-1, its application will become more common.

Reference:
Patent; Imperial Chemical Industries PLC; US5145856; (1992); A;,
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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.302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, molecular weight is 394.2783, as common compound, the synthetic route is as follows.Safety of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

A mixture of 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methyl phenyl) thiazole- 5 -carboxamide compound of formula-2 (50 gm), 2-(piperazin-l-yl)ethanol compound of formula-3 (82.5 gm) & 1 ,2-propanediol (750 ml) is expelled with nitrogen for 30 minutes. N,N- diisopropylethylamine (43.6 ml) was added to the reaction mixture and heated the reaction mixture to 115-120C. Stirred the reaction mixture for 8 hours at the same temperature. Cooled the reaction mixture to 25-30C and stirred for 6 hours at the same temperature. Filtered the precipitated solid and washed with 1 ,2-propanediol. Methanol (1300 ml) was added to the obtained wet compound and heated the reaction mixture to 65-70C. Stirred the reaction mixture for 2 hours at the same temperature. Filtered the reaction mixture at 65-70C and washed with methanol. Cooled the filtrate to 25-30C and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with methanol and dried to get the title compound. Yield: 38 gm; HPLC Purity: 99.57%, 0.01% (N-Oxide impurity), 0.09% (Deshydroxyethyl dasatinib); PXRD pattern of the obtained compound depicted in figure-5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; MADHUSUDHAN, Gutta; SEETHA RAMA SARMA, Peri; KHALIL AHAMED, Mogal; (38 pag.)WO2017/2131; (2017); A1;,
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Synthetic Route of 10132-07-7 , The common heterocyclic compound, 10132-07-7, name is 4-Amino-2,6-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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 solution of piperidinyl-4-methylamine (3.6 g) and N-tert-butoxycarbonylimidazole (5.3 g) in toluene (80 mL) was stirred at 25 C. overnight. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/2) to give Intermediate 227-I (4.7 g) in a 70% yield. Intermediate 227-I (4.7 g) and Et3N (2.7 mL) in 1-pentanol (20 mL) was reacted with 2,4-dichloro-6-aminopyrimidine (5.4 g) at 120 C. for 12 hours. After the solvent was removed, the residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/9) to afford Intermediate 227-II (5.2 g) in a 70% yield. A solution of Intermediate 227-II (1.0 g) treated with 1 M HCl (20 mL) in CH2Cl2 (10 mL) was stirred at room temperature for 8 hours. After the solution was concentrated, the resultant residue was neutralization with NH4OH, and extracted with CH2Cl2. The organic layer was separated and concentrated. The residue thus obtained was purified by column chromatography on silica gel (using MeOH as an eluant) to afford Intermediate 227-III (636 mg) in a 90% yield. Intermediate 222-III (790 mg) prepared from Example 222 was added to a solution of Intermediate 227-III (450 mg) in MeOH (20 mL). The mixture was stirred at 25 C. for 2 hours. NaBH(OAc)3 (2.0 g) was then added at 25 C. for 12 hours. After the solution was concentrated, a saturated aq. NaHCO3 solution was added to the resultant residue. The mixture was then extracted with CH2Cl2. The organic layer was separated and concentrated. The residue thus obtained was purified by column chromatography on silica gel (using MeOH as an eluant) to afford Intermediate 227-IV (539 mg) in a 60% yield. N1-Morpholine-N1-piperazine ethane (240 mg) was added to a solution of Intermediate 227-IV (160 mg) in 1-pentanol (1 mL). The mixture was stirred at 120 C. for 8 hours. The solution was concentrated and the residue was purified by column chromatography on silica gel (EtOAc/MeOH=5/1) to afford Intermediate 227-V (85 mg) in a 40% yield. A solution of 20% TFA/CH2Cl2 (1 mL) was added to a solution of Intermediate 227-V (85 mg) in CH2Cl2 (1 mL). The reaction mixture was stirred for 8 hours at room temperature and concentrated by removing the solvent. The resultant residue was purified by column chromatography on silica gel (21% NH3 (aq)/MeOH=1/19) to afford Compound 227 (65 mg) in a 90% yield. Compound 227 was then treated with 1 M HCl (1 mL) in CH2Cl2 (1 mL) for 0.5 hour. After the solvents were removed, the residue was treated with ether and filtered to give hydrochloride salt of Compound 227. CI-MS (M++1): 544.4.

The synthetic route of 10132-07-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yen, Chi-Feng; Hu, Cheng-Kung; Chou, Ming-Chen; Tseng, Chen-Tso; Wu, Chien-Huang; Huang, Ying-Huey; Chen, Shu-Jen; King, Chi-Hsin Richard; US2006/281712; (2006); A1;,
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Electric Literature of 120747-84-4, Adding some certain compound to certain chemical reactions, such as: 120747-84-4, name is 2-Aminopyrimidine-5-carbaldehyde,molecular formula is C5H5N3O, 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 120747-84-4.

Sodium triacetoxy borohydride (883 mg, 4.166 rnmol) was added slowly at 0 C to a solution of (trans)-2-(4-(benzyloxy)phenyl)cyclopropanamine (Intermediate B, 500 mg, 2.083 mmol), 2-aminopyrimidine-5-carbaldehyde (256 mg, 2.083 mmol) in DCE (10 mL) and stirred for 20 h. After completion, the solvent was evaporated. The residue was dissolved in Methanol (15 mL), NaBH4 (237 mg, 6.249 mmol) was added slowly at 0 C and stirred for 3 h. After completion, the solvent was evaporated, the residue was dissolved in ice water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic layers were washed with brine (20 mL) and dried over anhydrous Na2S04; filtered and evaporated. The crude residue was purified by prep HPLC to afford 5-(((tran_?)-2-(4- (benzyloxy)phenyl)cyclopropylamino)methyl)pyrimidin-2-amine (180 mg, 25 %) as white solid. .H-NMR (400 MHz, DMSO-d6) delta (ppm): 0.85 (q, 1H), 0.90 (quin, 1H), 1.73 (m, 1H), 2.07 (m, 1H), 2.75 (brs, 1 H), 3.53 (s, 2H), 5.04 (s, 2H), 6.46 (s, 2H), 6.85 (d, 2H), 6.92 (d, 2H), 7.33 (m, 1H), 7.42 (m, 4H), 8.1 1 (s, 2H). Mass (M+H): 347.3

According to the analysis of related databases, 120747-84-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORYZON GENOMICS S.A.; ORTEGA MUNOZ, Alberto; FYFE, Matthew, Colin, Thor; MARTINELL PEDEMONTE, Marc; TIRAPU FERNANDEZ DE LA CUESTA, Inigo; ESTIARTE-MARTINEZ, Maria de los Angeles; WO2012/13728; (2012); A1;,
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Reference of 39876-88-5, 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 39876-88-5, name is 4-Chlorobenzofuro[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

N-(3-(9H-carbazol-3-yl)phenyl)-N-phenyldibenzo[b,d]furan-2-amine (2.5 g, 5.0 mmol) and sodium hydride (0.34 g, 8.5 mmol) were mixed in 30 mL of dry DMF. The solution was stirred for 1 hour at room temperature. 4-chlorobenzofuro[3,2-d]pyrimidine (1.9 g, 9.5 mmol) was added. The mixture was stirred overnight under nitrogen. The reaction mixture was poured into water and the precipitate was filtered. The residue was then purified by column chromatography using THF:hexane (1:3, v/v) as the eluent. 2.4 g (74%) of a pale yellow solid was obtained as the product.

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 39876-88-5, 4-Chlorobenzofuro[3,2-d]pyrimidine.

Reference:
Patent; Universal Display Corporation; Joseph, Scott; Kwang, Raymond; Lee, Chi Hang; Shia, Chuan Jun; Ram, SiV Cheung; (131 pag.)KR2015/9461; (2015); A;,
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Reference 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 (1 -(3-(difluoromethyl)phenyl)-5-methyl-1 H-i 2,3- triazol-4-yl)methanol (45 mg, 0.19 mmol) stirring in THF (1 mL) was added NaH (60percent dispersion in mineral oil, 22.6 mg, 0.56 mmol) and the reaction wasstirred for 5 mi 2-Chloro-5-methoxypyrimidine was then added and the reaction was stirred at rt for 1 h. The reaction was quenched with H20, then diluted with EtOAc and H20. The layers were separated and the aqueous layer was extracted with EtOAc (3X). The combined organic layers were washed with H20 (ix), brine (ix), then dried (Na2504) and concentratedunder reduced pressure. Purification (FCC, 5i02, EtOAc/hexanes 0 – 60percent)afforded the title compound (41 mg, 62percent). MS (ESI): mass calcd. forC15H15F2N502, 347.1; m/zfound, 348.0 [M+H]. 1H NMR (400 MHz, CDCI3) O8.24 (5, 2H), 7.71 ? 7.56 (m, 4H), 6.73 (t, J = 56.1 Hz, 1 H), 5.56 (5, 2H), 3.88(5, 3H), 2.45 (5, 3H).

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; JANSSEN PHARMACEUTICA NV; CHEN, Gang; CHROVIAN, Christa C.; COATE, Heather R.; DVORAK, Curt A.; GELIN, Christine F.; HISCOX, Afton; LETAVIC, Michael A.; RECH, Jason C.; SOYODE-JOHNSON, Akinola; STENNE, Brice; WALL, Jessica L.; ZHANG, Wei; (583 pag.)WO2017/139428; (2017); A1;,
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Electric Literature of 1088994-22-2, 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.1088994-22-2, name is 5-Methyl-2-(pyrimidin-2-yl)benzoicacid, molecular formula is C12H10N2O2, molecular weight is 214.22, as common compound, the synthetic route is as follows.

To a solution of 5-methyl-2-(pyrimidin-2-yl)benzoic acid(0.040 g, 0.19 mmol) in CHCl3 (1.5 mL) were added DIPEA(0.092 ml, 0.53 mmol), 43d (0.037 g, 0.15 mmol) and a solution of1-propanephosphonic acid cyclic anhydride (T3P, 1.7 mol/L inEtOAc, 0.30 ml, 0.52 mmol) at room temperature. After this mixturewas stirred at 60 C for 5 h, water was added, and the mixturewas extracted with CHCl3. The organic layer was washed withbrine, dried over Na2SO4, filtered, and concentrated under reducedpressure. The resulting residue was purified by preparative HPLC toobtain the titled compound 12 as a colorless amorphous (0.024 g,36% yield). HRMS (ESI/APCI dual) for C24H24FN6O2 [M+H]+, calcd:447.1939, found: 447.1923; LC-MS t = 0.87 min, [M+H]+ = 447.Please see the Supplementary data for pictures of 500 MHz 1Hand 125 MHz 13C NMR spectra in CDCl3 at 25 C.

Statistics shows that 1088994-22-2 is playing an increasingly important role. we look forward to future research findings about 5-Methyl-2-(pyrimidin-2-yl)benzoicacid.

Reference:
Article; Futamura, Aya; Nozawa, Dai; Araki, Yuko; Tamura, Yunoshin; Tokura, Seiken; Kawamoto, Hiroshi; Tokumaru, Yuichi; Kakihara, Sora; Aoki, Takeshi; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5203 – 5215;,
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