Pyrimidines

Related Products of 69034-12-4, 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 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step A: (2S,3R)-tert-butyl 2-methyl-3-((5-(trifluoromethyl)pyrimidin-2-yl)oxy)piperidine-1-carboxylate. To (2S,3R)-tert-butyl 3-hydroxy-2-methylpiperidine-1-carboxylate (670 mg, prepared according to J. Org. Chem. 2008, 73, 2898) in THF (15 mL) at 0 C. was added NaH (60 wt %, 188 mg). After 15 min, 2-chloro-5-(trifluoromethyl)pyrimidine (570 mg) was added and the reaction allowed to proceed at rt overnight. The reaction was diluted with H2O and extracted with DCM. The organic layers were dried (MgSO4). Purification via silica gel chromatography (0-40% EtOAc in heptane) gave the title compound (813 mg, 72%).

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 69034-12-4, 2-Chloro-5-(trifluoromethyl)pyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Dvorak, Curt A.; Shireman, Brock T.; US2014/275095; (2014); A1;,
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Pyrimidine – Wikipedia

Related Products of 5413-85-4 , The common heterocyclic compound, 5413-85-4, name is 5-Amino-4,6-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.

Example 144; N-(4-Ethoxypyrimidin-5-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (4) 4-Ethoxypyrimidine-5-amine; A mixture of 5-amino-4,6-dichloropyrimidine (5.00 g, 30.5 mmol), tetrahydrofuran (100 ml), sodium hydroxide (2.44 g, 61.0 mmol), ethanol (100 ml) and 10% palladium-carbon (500 mg) was stirred under a hydrogen atmosphere at room temperature for 1 day, insolubles were filtered off and an organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to obtain the desired product (4.00 g, 94.3%) as an oil. 1H-NMR (CDCl3) delta; 1.43 (3H, t, J = 6.9 Hz), 3.75 (2H, br s), 4.48 (2H, q, J = 6.9 Hz), 7.92 (1H, s), 8.24 (1H, s).

The synthetic route of 5413-85-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
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Related Products of 36315-01-2, 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. 36315-01-2, name is 2-Amino-4,6-dimethoxypyrimidine. A new synthetic method of this compound is introduced below.

STR1346 A mixture of 15.5 g (0.1 mole) of 2-amino-4,6-dimethoxy-pyrimidine, 13.1 g (0.1 mole) of ethoxycarbonyl isothiocyanate and 200 ml of acetonitrile is stirred for 2 hours at 60 C. Thereafter, the mixture is cooled to 10 C., and the crystalline product obtained is isolated by filtration with suction. 22.5 g (79% of theory) of 1-(ethoxycarbonyl)-3-(4,6-dimethoxy-pyrimidin-2-yl)-thiourea of melting point 194 C. (decomposition) are obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36315-01-2, 2-Amino-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Aktiengesellschaft; US4840661; (1989); A;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile, 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, name: 2,4-Dichloropyrimidine-5-carbonitrile, blongs to pyrimidines compound. name: 2,4-Dichloropyrimidine-5-carbonitrile

Followingthe preparation protocol of Section 5.1.2.1, the reaction mixtureof 2,4-dichloropyrimidine-5-carbonitrile (8d) (367 mg, 2.0mmol), K2CO3 (552 mg, 4.0 mmol) and phenol (188 mg, 2.0 mmol)in acetone (10 mL) was stirred at room temperature for 7 h to givecompound 9f as a white solid (408 mg, 88.0percent); mp 94?96 C; 1HNMR (400 MHz, Acetone d6) d (ppm) 9.08 (s, 1H), 7.54 (t, J = 7.2Hz, 2H), 7.41?7.35 (m, 3H); HRMS (ESI): m/z, Calcd. for C11H7ON3-Cl [M+H]+: 232.0272, Found 232.0270

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Cui, Guonan; Jin, Jing; Chen, Hualong; Cao, Ran; Chen, Xiaoguang; Xu, Bailing; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2186 – 2197;,
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Synthetic Route of 146533-41-7, 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. 146533-41-7, name is 5-(4-Bromophenyl)-4,6-dichloropyrimidine. A new synthetic method of this compound is introduced below.

600 ml of DMSO was added to 6.4 g of Sodium hydroxide, 100 g of reacting 5-(4- bromophenyl)-4,6dichloropyrimidine, followed by 116 g of N-propyl sulfomyl amide potassium salt (Sodium salt can also be used). The reaction mixture was stirred at 40±5 C for 6 hrs. On completion of the reaction, the reaction mass was cooled to 27±2 C and 1000 ml of purified water was added. The pH was adjusted with IN HC1 solution, followed by filtration. Wet cake was further treated with purified water and heated at 50±2 C for 30 minutes, cooled at 27±2 C. The solid was filtered, washed with purified water. The water slurry wet material was further subjected to methanol purification, heated at 50±2 C for 30 mins, cooled at 27±2 C. The final solid obtained was washed with methanol and dried under vacuum at 43±2 C for 12 hours.Dry weight: 115g

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,146533-41-7, its application will become more common.

Reference:
Patent; CIPLA LIMITED; KING, Lawrence; RAO, Dharmaraj Ramachandra; MALHOTRA, Geena; PATHI, Srinivas Laxminarayan; PUPPALA, Ravikumar; KOMMULA, Narayanaswami; (29 pag.)WO2017/33016; (2017); A1;,
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Electric Literature of 56843-79-9, 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 56843-79-9, name is 4-Chloro-2-methylthieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A clear solution of 4-chloro-2-methylthieno[2,3-djpyrimidine (30 mg, 0.l62mmol), 4,4,4- trifluorobutylamine (55 tL, 0.486 mmol), DIEA (35 tL, 0.20 mmol), and dry p-dioxane (0.5 mL) was heated at 140 C for 90 minutes in a microwave reactor. A yellow solution formed, which was partitioned between DCM and water. The DCM layer was separated and set aside, and the aqueous layer was washed with ethyl acetate. Both organic layers were combined and concentrated undervacuum to afford a viscous yellow substance, which was lyophilized for 2 hours to give the final product(37 mg, 83% yield). LC-MS analysis indicated the desired product with >97% purity and mass: m/z 276(M+H). Calcd for C11H12F3N3S=275.29. 1H NMR (400MHz, DMSO-d6) oe 7.87 (t, J = 5.4 Hz, 4 H), 7.53(d, J = 5.9 Hz, 5 H), 7.43 (d, J = 5.9 Hz, 1 H), 3.60 – 3.51 (m, 10 H), 2.43 (s, 3 H), 2.40 -2.30 (m, 9 H),1.93 – 1.74 (m, 10 H).

According to the analysis of related databases, 56843-79-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAINT LOUIS UNIVERSITY; WASHINGTON UNIVERSITY; MEYERS, Marvin, J.; SINGH, Megh; STALLINGS, Christina, L.; WEISS, Leslie, A.; WILDMAN, Scott; ARNETT, Stacy, D.; (134 pag.)WO2019/18359; (2019); A1;,
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Pyrimidine – Wikipedia

Related Products of 10397-13-4, 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 10397-13-4 as follows.

A mixture of compound 1-b (1.4 g, 6 mmol), methyl 2-(methylsulfonyl) acetate (1.0 g, 6.6 mmol), sodium hydride (500 mg, 12 mmol) and dimethylsulfoxide (30 mL) was added to a sealed tube and stirred at 120C under microwave for 15 minutes. The reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. The combined organic phase was separated and concentrated under reduced pressure to give crude product which was purified by Combi-flash column chromatography to give compound 1-c (500 mg). Purity: 95%. Spectrum data: MS m/z(ESI): 350[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,10397-13-4, its application will become more common.

Reference:
Patent; Shanghai Haiyan Pharmaceutical Technology Co., Ltd.; Yangtze River Pharmaceutical Group Co., Ltd.; SHEN, Sida; NI, Xiaojing; ZHANG, Zhiyuan; YANG, Zheng; HE, Xiangyu; WANG, Weiwei; ZHOU, Fusheng; (74 pag.)EP3235816; (2017); A1;,
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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.22536-66-9, name is 2-Chloropyrimidine-4-carboxamide, molecular formula is C5H4ClN3O, molecular weight is 157.5578, as common compound, the synthetic route is as follows.Quality Control of 2-Chloropyrimidine-4-carboxamide

Example 261 N-[10,ll-dimethyl-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02’6]dodeca- l(12),6,8,10-tetraen-3-yl]-2-[(2-methoxyethyl)amino]pyrimidine-4-carboxamide (ABR 239626) To a stirred solution of 2-chloropyrimidine-4-carboxamide, available via a literature method: PCT Int. AppL, 2001068612 (330 mg, 2.08 mmol) in DMF (6 mL) was added methyl 3,3,3- trifiuoro-2-oxopropanoate (355 mu, 3.47 mmol) followed by pyridine (170 mu, 2.08 mmol) under nitrogen. The reaction was stirred at room temperature for 2 h. Thionyl chloride (150 mu, 2.08 mmol) was added at 0C. The reaction was stirred for 1 h at 0C and then concentrated. The residue was filtered through a short pad of silica, eluting with DCM, under nitrogen. The filtrate was concentrated, and the acyl intermediate that remained was dissolved in DMF (5 mL) under nitrogen. The solution of acyl intermediate was added to a solution of 5,6-dimethyl-lH-l ,3- benzodiazol-2 -amine (280 mg, 1.74 mmol) in DMF (8 mL) followed by triethylamine (280 2.08 mmol). The reaction mixture was stirred for a further 16 h and then concentrated. The residue was dissolved in EtOAc (50 mL) and washed with water (3 x 50 mL) and brine (2 x 50 mL) and then dried (MgSO_i), filtered and concentrated to afford 2-chloro-N-[10,l 1 -dimethyl-4- oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3- yl]pyrimidine-4-carboxamide. (260 mg, 15%). m/z = 424.95 (MH)+. A sealable tube was charged with a portion of 2-chloro-N-[10,l 1 -dimethyl-4-oxo-3- (trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3-yl]pyrimidine-4- carboxamide (250 mg, 0.35 mmol), 2-methoxyethan- 1 -amine (92 muL·, 1.06 mmol), K2C03 (150 mg, 1.06 mmol) and DMF (5 mL). The tube was flushed with nitrogen, sealed and stirred at 100C for 6 h. Then reaction mixture was concentrated and the resulting residue was diluted with EtOAc (20 mL) and water (20 mL). The aqueous phase was extracted with EtOAc (2 x 10 mL). The combined organic extracts were washed with 10 % citric acid (aq) (2 x 20 mL) and brine (20 mL) and then dried (MgS04), filtered and concentrated. The crude product was purified by automated reverse phase HPLC (low pH Method A) to afford the title compound as a white solid (50 mg, 31 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-66-9, 2-Chloropyrimidine-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ACTIVE BIOTECH AB; WELLMAR, Ulf; LIBERG, David; EKBLAD, Maria; BAINBRIDGE, Marie; EAST, Stephen; HARGRAVE, Jonathan; PREVOST, Natacha; WO2015/177367; (2015); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 764659-72-5, 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.764659-72-5, name is (2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate, molecular formula is C18H26FN3O4S, molecular weight is 399.4802, as common compound, the synthetic route is as follows.

EXAMPLE-13: Synthesis of 4-amino-5-fluoro-1-(2 ?-hydroxymethyl-[1,3]-oxothiolane- 5S-yl)1tf-pyrimidin-3-one. 2-fluorobenzoic acid salt (formula-8b1); Dipotassium hydrogen orthophosphate (83.3 g) was dissolved in a mixture of industrially methylated spirit (IMS, 600 mL) & purified water (200 mL) and the obtained solution was cooled to 18C. The compound of formula-7b (100 g, 0.26 mol) was added at 15-22C and the suspension was stirred at 18-22C for 1 h. A solution of sodium borohydride (20. 4 g (0.54 mol) in water (110 mL) containing sodium hydroxide (40 mg)) was added drop wise by keeping temperature at 18-22C and maintained for 4 h. The completion of the reaction was confirmed by TLC. The reaction mass was transferred into a separating funnel and the layers were separated. The organic layer pH was adjusted to 5.9-6.3 with aq. HCI (~25 mL) and readjusted to pH 7.5-7.8 with sodium hydroxide (15 mL, 15% w/w) and filtered. IMS (~790 mL) was distilled out initially atmospherically followed by reduced pressure to reduce the traces of IMS. The resultant residue was diluted with water (200 mL) and then cooled to 22-30C. Toluene (150 mL) was added to the reaction mass under stirring, allowed the layers to settle and separate the layers. Toluene layer was washed with water (100 mL) and combined aqueous layer was charcoalized. The filtrate was warmed to 38-42C, 2- fluorobenzoic acid (37 g, 0.26 mol) was added and stirred for 2h at the same temperature. The reaction mass was cooled to 22-30C and maintained for 3-4h. The separated solid was filtered and washed with pre-cooled water and dried to get compound of formula-8b. in 80 g. 1H NMR (300 MHz, DMSO-d6): delta 13.40 (brs, 1H), 8.20 (d, 1 H, J=7.2 Hz), 7.84-8.00 (m, 2H), 7.58-7.68 (m, 2H), 7.28-7.34 (m, 2H), 6.12-6.16 (m, 1H), 5.41 (t, 1 H, J=5.4 Hz), 5.18-5.20 (t, 1 H, J=3.9 Hz), 3.70 -3.82 (m, 2H), 3.39-3.45 (m, 1H), 3.09-3.15 (dd, 1 H, J=11.85 & 4.35 Hz).

Statistics shows that 764659-72-5 is playing an increasingly important role. we look forward to future research findings about (2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate.

Reference:
Patent; MATRIX LABORATORIES LTD.; RAMA, Shankar; GORANTLA, Sarat, Chandra, Srikanth; VADALI, Lakshmana, Rao; INUPAKUTIKA, Venkata, Bala, Kishore, Sarma; DASARI, Srinivas, Rao; MITTAPELLY, Nagaraju; SINGH, Santosh, Kumar; DATTA, Debashish; WO2011/95987; (2011); A1;,
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Pyrimidine – Wikipedia

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.88474-31-1, name is 4-Chloro-6-methoxy-2-methylpyrimidin-5-amine, molecular formula is C6H8ClN3O, molecular weight is 173.6, as common compound, the synthetic route is as follows.Quality Control of 4-Chloro-6-methoxy-2-methylpyrimidin-5-amine

Example 3: coupling of 5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine and Nacetylimidazolidinone in the presence of an excess amount of acid catalyst and Na2CO3 as a base – scale up alternative.5-am ino-4-methoxy-6-chloro-2-methyl-pyrim idine (20.Ograms, 11 5mmol) and Nacetylimidazolidinone (14.7 grams, ll5mmol) were dissolved in anhydrous DMSO and anhydrous sodium carbonate (37.5 grams, 354mmo1, 3.0 equivalents) was added. The reaction flask was cooled in ice-salt-acetone mixture and POCI3 was added dropwise in 2.5 hour keeping temperature be?ow 5C. After the addition the ice bath was removedand the flask was stirred at 58-60C under nitrogen for 2 days. A small sample was taken and analysed by HPLC. There was no starting material and the product was formed. Workup: The reaction mixture was quenched by slowly pouring in crushed ice. The product precipitated and the product was filtered and dried under vacuum. Without any further purification the product was used in the next step to generate crude moxonidine. Yield: 31.7 grams (82.9%). Mass spec.: 283 (m+) 5 grams of the product obtained in example 3 was taken in 20m1 isopropanol andisopropyl alcohol-HCI (lOmI) was added. The resulting mixture was stirred at ambient temperature for 8 hours. The hydrochloride salt was precipitated and was then filtered and dried. The salt was dissolved in water and basified to pH 9.0. The product was extracted in ethyl acetate. Organic layer containing product was washed by water, brine solution and dried over anhydrous Na2SO4. Sodium sulfate was filtered off thesolvent was distilled out to get the crude 4-Chloro-6-methoxy-2-methyl-5-(2-imidazolin-2-yl)aminopyrimidine (free base). Yield: 2.6 grams (72%). Mass spec.: 242 (m+) (see spectra of Fig. ito 3). NMR: see Fig. 4 for 13C NMR spectrum and Fig. 5-6 for 1H NMR spectra.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88474-31-1, 4-Chloro-6-methoxy-2-methylpyrimidin-5-amine, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT HEALTHCARE PRODUCTS BV; ABBOTT LABORATORIES; ACQUASALIENTE, Maurizio; LAGERWEIJ, Gert; DESHPANDE, Mahendra; SHAH, Rajendra; WO2015/11010; (2015); A1;,
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