Tag: M.W:200-300

Electric Literature of 955368-90-8 ,Some common heterocyclic compound, 955368-90-8, molecular formula is C9H10N4OS, 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.

Compound 51-1 (2.00 g, 9.90 mmol) and Intermediate I1 (2.20 g, 9.90 mmol) were added into 1,4-dioxane solution, then N,N’-diethylethylenediamine (1.27 g, 10.89 mmol), potassium carbonate (1.37 g, 9.90 mmol) and cuprous iodide (1.89 g, 9.90 mmol) were added sequentially under nitrogen atmosphere, the temperature was raised to 95C and the reaction was stirred at reflux for 12 hours until it was complete. Then the mixture was cooled down to r.t. and concentrated, quenched by 50 mL water, then extracted by 50 mL EA, the organic phase was washed by 50 mL saturated brine, dried over anhydrous sodium sulfate, then filtered, evaporated and purified by chromatography (EA /PE =1/10-1/4) to give 51-2. 1H NMR (400MHz, CDCl3) delta 8.90 (s, 1H), 7.75 -7.71 (m, 1H), 7.35 (d, J=8.0 Hz, 1H), 6.67 (d, J=8.2 Hz, 1H), 5.71 – 5.64 (m,1H), 5.04 (dd, J=10.0 Hz, 1H), 5.05 – 4.80 (m,1H), 4.81 (d, J=6.4 Hz, 1H), 4.34 -4.29 (m, 2H), 2.55 (s, 3H), 1.56 (d, J=2.4 Hz, 1H), 1.42 – 1.38 (m, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,955368-90-8, its application will become more common.

Reference:
Patent; Shijiazhuang Sagacity New Drug Development Co., Ltd.; QIAN, Wenyuan; YANG, Chundao; LI, Zhengwei; LI, Jie; LI, Jian; CHEN, Shuhui; (137 pag.)EP3572413; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Chloro-4,6-diphenylpyrimidine

20 g (48.7 mmol) of the intermediate 1-4 was dissolved in 0.17 L of tetrahydrofuran (THF) under a nitrogen atmosphere, 13.0 g (48.7 mmol) of 2-chloro-4,6-diphenylpyrimidine and 1.69 g (1.46 mmol) of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was agitated. 16.8 g (122 mmol) of potassium carbonate saturated in water was added thereto, and the obtained mixture was heated and refluxed at 80 C for 6 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and treated with anhydrous MgSO4 to remove moisture and then, filtered and concentrated under a reduced pressure. Then, a residue obtained therefrom was separated and purified through flash column chromatography, obtaining 22.8 g (91 %) of the compound 2. (0170) HRMS (70 eV, EI+): m/z calcd for C37H26N2O: 514.2045, found: 514. (0171) Elemental Analysis: C, 86 %; H, 5 %

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, 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine.

Reference:
Patent; Cheil Industries Inc.; LEE, Han-Ill; YU, Eun-Sun; KANG, Dong-Min; KANG, Eui-Su; MIN, Soo-Hyun; YANG, Yong-Tak; OH, Jae-Jin; RYU, Dong-Kyu; LEE, Sang-Shin; JANG, Yu-Na; JEONG, Soo-Young; JO, Young-Kyoung; HAN, Su-Jin; HONG, Jin-Seok; EP2952511; (2015); 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. 13162-26-0, name is 2,4-Dichloro-6-methyl-5-nitropyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 13162-26-0

To a solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (7 g, 34 mmol) and CH3COOK (9.8 g, 100 mmol) in MeOH (150 mL) was added Pd C (3 g). The mixture was stirred at H2 atmosphere for overnight. The reaction mixture was filtered, and the solvent was concentrated under reduced pressure to give the product 4-methylpyrimidin-5 -amine (1.5 g, 43%), which was used to next step without furthermore purification. ‘HNMR: MeOD 400MHz ? 8.28(s, 1H), 8.04(s, 1H), 2.3 l(s, 3H).

The synthetic route of 13162-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); 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. 56686-16-9, name is 5-Bromo-2,4-dimethoxypyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 56686-16-9

Step 46.7: Di-tert-butyl 1-(2,4-dimethoxypyrimidin-5-yl)hydrazine-1,2-dicarboxylate To a stirred solution of 5-bromo-2,4-dimethoxypyrimidine (400 g, 1.826 mol) in anhydrous 52 THF (3 L) under argon and cooled down to 0 C. was added dropwise TurboGrignard (1.821 L, 2.367 mol). The resulting mixture was stirred at 0 C. until exothermic ceased then, allowed to warm up and stir at RT for 30 min. A solution of di-tert-butyl azodicarboxylate in anhydrous THF (1 L) was added dropwise to the mixture and the reaction was stirred at RT for 1 hr. The reaction was slowly quenched with a saturated aq. NH4Cl solution (2 L), diluted with EtOAc (2 L) and water (2 L) and both phases separated. The aq. phase was extracted with EtOAc (3 L), combined organic layers were washed with brine (3 L), dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting yellow oil was dissolved in Hexane (3 L) and the suspension was stirred at 0 C. for 3 hr, filtrated off and dried to afford a first batch of white crystals. The mother liquor was concentrated under reduced pressure and purified to afford a second batch of white crystals. The two batches were combined to afford the title product (507 g, 1.369 mol, 75% yield) as white crystals. tR: 1.03 min (LC-MS 1); ESI-MS: 371 [M+H]+, ESI-MS: 369 [M-H]- (LC-MS 1).

The synthetic route of 56686-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; US2014/349990; (2014); 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. 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, the common compound, a new synthetic route is introduced below. Recommanded Product: 130049-82-0

300 ml of acetonitrile was charged followed by 20.0 g of 3-(2-chloroethyl)-9-hydroxy-2- methyl-6,7,8,9-tetrahydro-4H-pyrido-[1 ,2-a]-pyrimidin-4-one and 21.0 g of 6-fluoro-3-(4- piperidinyl)-1 ,2-benzisoxazole hydrochloride at room temperature. The reaction mass was stirred at room temperature for 5 minutes and 20.0 g of potassium carbonate and 0.7 g of potassium iodide were charged. Further, 0.2 g of sodium borohydride was charged and the temperature was raised to 65+/-2C. The reaction mass was maintained at 65+/-2C for 25 hours. After reaction completion, the reaction mass was slowly cooled to room temperature. The solids were filtered, washed with 50 ml of acetonitirle and then dissolved in 800 ml of methylene chloride at room temperature. The contents were heated to 30-35C, maintained for 10 minutes, filtered and washed with 20 ml of methylene chloride. The clear filtrate was distilled completely under vacuum below 35C and replaced with 50 ml of acetone. Further, 300 ml of acetone was charged, heated to 45C and stirred for 30 minutes. The reaction mass was cooled to room temperature and stirred for 1 hour. The product was filtered, washed with 20 ml of acetone and dried under vacuum at 50-55C to yield paliperidone (30 g, yield : 150% w/w, efficiency : 85. 1 %, keto impurity by HPLC : 0.01%, total impurity level by HPLC: 1.0 %)

The synthetic route of 130049-82-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CIPLA LIMITED; PUPPALA, Ravikumar; PATHI, Srinivas, Laxminarayan; KANKAN, Rajendra, Narayanrao; COTTRILL, Emily, Elizabeth, Helen; WO2012/164242; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26830-94-4, Adding some certain compound to certain chemical reactions, such as: 26830-94-4, name is 2,6-Dichloropyrimidine-4-carbonyl chloride,molecular formula is C5HCl3N2O, 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 26830-94-4.

To a solution of Compound 2 (26.13 g, 123.6 mmol) in Et20 (500 mL) was added a mixture of 0.5 M NH3 in dioxane (250 mL, 125 mmol) and DIPEA (22 mL, 126 mmol) dropwise over 50 min. After stirring at RT overnight the reaction mixture was concentrated in vacuo to give a residue that was purified by flash chromatography (Si02, 10-50% EtOAc/hexanes). The product obtained was triturated with 10 mL 10% EtOAc/hexanes and filtered to give 9.74 g (41%) of Compound 3 as an orange crystalline solid. ]H NMR (400 MHz, DMSO-d6): delta 8.40 (br s, 1H), 8.16 (br s, 1H), 8.10 (s, 1H). LC/MS: m/z= 192 [M+H]+ (Calc: 191).

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. 26830-94-4, 2,6-Dichloropyrimidine-4-carbonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PURDUE PHARMA L.P.; LYNCH, Stephen, M.; WO2015/112801; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 85426-79-5, 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. 85426-79-5, name is 4-Chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C6H5ClN4S, 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.

Step 3. Preparation of6-Methylsulfanyl-lH-pyrazolo[3,4-d]pyrimidine; EPO 4-Chloro-6-methylsulfanyl-lH-indazole (11.02 g, 0.0549 mol) was disolved in a mixture of 160 niL THF and 350 mLMeOH, and TFA (7.66 mL, 0.055 mol) was added. While the reaction mixture was stirred at RT under argon, palladium on activated carbon (2.0 g of 10% Pd, 0.001 mol) was added. The reaction mixture was stirred under H2 atmosphere for two hours, after which the reaction flask was flushed with argon, and another 2.0 g of palladium on activated carbon was added to the reaction mixture. The reaction mixture was again stirred for two hours under H2, after which the flask was purged with argon, another 2.0 g of palladium on activated carbon was added, and the reaction mixture was stirred for 64 hours under hydrogen. The reaction mixture was filtered through Celite, and the Celite pad was washed twice with 200 mL of warm MeOH and twice with 200 mL of warm methylene chloride. The combined organic phases were evaporated under reduced pressure. The residue was suspended in water, filtered, and the filter cake was suspended in heptane, filtered, and dried to yield 5.36 g of 6-Methylsulfanyl-lH-pyrazolo[3,4-d]pyri- midine. Mass Spec. M+H = 167.

According to the analysis of related databases, 85426-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2007/23105; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 74901-69-2, Adding some certain compound to certain chemical reactions, such as: 74901-69-2, name is 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine,molecular formula is C6H4Cl2N2S, 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 74901-69-2.

5.4 (S)-5-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-1-methylpiperidin-2-one (III-5): 0.27 g (II) are placed in 3 ml dioxane, then first 0.45 ml diisopropylethylamine, then 0.25 g (S)-5-amino-1-methylpiperidin-2-one are added. The reaction mixture is heated to 130 C., until there is no further reaction, and cooled, then evaporated down. The product is extracted with dichloromethane and purified by chromatography (preparative HPLC, method A). 0.26 g (III-5) are obtained as a solid. Analytical HPLC-MS (method A): RT=1.06 min.

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. 74901-69-2, 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21501; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 109229-22-3, 6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one, 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, Recommanded Product: 109229-22-3, blongs to pyrimidines compound. Recommanded Product: 109229-22-3

INTERMEDIATE 26-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido [4,3-d] pyrimidine[00274] A mixture of 6-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one (5.0 g,0.02 mol), phosphoryl chloride (3.30 mL, 0.035 mol) and acetonitrile (80 mL) and DMF (catalytic amount) was heated at 70 0C for 1 hour. The mixture was concentrated in vacuo and the remaining black residue was taken up in dichloroniethane (250 mL) and poured over ice. The mixture was carefully neutralized with the addition of solid sodium bicarbonate. The organic layer was separated and dried over sodium sulfate and concentrated in vacuo. The mixture was purified by silica gel column with EtOAc/hexane (0-100%) to yield the title compound as a yellow oil (3 g, 57.8%). MS: 260 [M+l]+; 1H NMR (400 MHz, DMSO-d6): 8.80 (s, IH), 7.40-7.24 (m, 5H), 3.76 (s, 2H), 3.57 (s, 2H), 2.92 (t, 2H), 2.80 (t, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109229-22-3, 6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; RENOVIS, INC.; WO2008/123963; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1780-42-3, 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. 1780-42-3, name is 2,4,6-Trichloro-5-isopropylpyrimidine, molecular formula is C7H7Cl3N2, 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 A 2,4-Dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine (2): To a stirred mixture of 5-isopropyl-2,4,6-trichloropyrimidine (1) (23.68 g, 0.105M), 3,5-dimethylphenol (12.2 g, 0.2M) in anhydrous DMF (200 ml) cooled in a dry ice-acetone bath (-40 C.) under nitrogen atmosphere, was portionwise added 60% sodium hydride (4.2 g, 0.105M). The reaction temperature was then slowly raised to room temperature during 3 hr. The reaction mixture was then diluted with ether, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a crude product as a pale yellow solid. The crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:9)) to afford 28 g (90%) of a white solid. m.p. 107-108 C.; 1H NMR (200 MHz, CDCl3) delta 1.40(6H, d, J=7.0 Hz), 2.35 (6H, s), 3.58 (1H, m), 6.72 (2H, s), 6.91 (1H, s). 2,4-Dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine (65):; To a stirred mixture of 2,4,6-Trichloro-5-isopropyl-pyrimidine (23.68 g, 0.105M), 3,5-dimethylphenol (12.2 g, 0.2M) in anhydrous DMF (200 ml) cooled in a dry ice-acetone bath (-40 C.) under nitrogen atmosphere, was portionwise added 60% sodium hydride (4.2 g, 0.105M). The reaction temperature was then slowly raised to room temperature during 3 hr. The reaction mixture was then diluted with ether, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a crude product as a pale yellow solid. The crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:9)) to afford 28 g (90%) a white solid. m.p. 107-108 C.; 1H NMR (200 MHz, CDCl3) delta 1.40(6H, d, J=7.0 Hz), 2.35 (6H, s), 3.58 (1H, m), 6.72 (2H, s), 6.91 (1H, s).; Preparation Method of 3-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-phenyl]-acrylonitrile; 2,4-Dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine:; To a stirred mixture of 5-isopropyl-2,4,6-trichloropyrimidine (23.68 g, 0.105M), 3,5-dimethylphenol (12.2 g, 0.2M) in anhydrous DMF (200 ml) cooled in a dry ice-acetone bath (-40 C.) under nitrogen atmosphere, was portionwise added 60% sodium hydride (4.2 g, 0.105M). The reaction temperature was then slowly raised to room temperature during 3 hr. The reaction mixture was then diluted with ether, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a crude product as a pale yellow solid. The crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:9)) to afford 28 g (90%) of a white solid. m.p. 107-108 C.; 1H NMR (200 MHz, CDCl3) delta 1.40 (6H, d, J=7.0 Hz), 2.35 (6H, s), 3.58 (1H, m), 6.72 (2H, s), 6.91 (1H, s).

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 1780-42-3, 2,4,6-Trichloro-5-isopropylpyrimidine.

Reference:
Patent; Guo, Hongyan; Kim, Choung U.; Kim, Hae Soo; Lee, Chong-Kyo; Lee, Ill Young; Mitchell, Michael L.; Son, Jong Chan; Xu, Lianhong; US2008/70920; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia