Tag: M.W:100-200

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.287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, molecular weight is 172.57, as common compound, the synthetic route is as follows.Recommanded Product: 287714-35-6

To a solution of 6-(tert-butylsulfonyl)-N-(5-fluoro-lH-indazol-3-yl)-7-(2-(piperazin-l- yl)ethoxy)quinolin-4-amine (120 mg, 0.23 mmol) in NMP (2 mL) was added methyl 2- chloropyrimidine-5-carboxylate (47 mg, 0.27 mmol), and sodium bicarbonate (57 mg, 0.68 mmol) and the reaction was stirred at 110 C for lh. The residue was subjected directly to purification by flash chromatography (30g pre-packed C-18 SNAP cartridge: 30% to 85% acetonitrile (0.1% ammonia) in water (10 mM ammonium bicarbonate)). The desired fractions were combined and concentrated to afford the title compound (106 mg, 0.16 mmol, 70 % yield). LCMS T= 1.15 min, ES+ve 663.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CASILLAS, Linda N.; HARLING, John David; MIAH, Afjal Hussain; SMITH, Ian Edward David; RACKHAM, Mark David; (204 pag.)WO2017/182418; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 893755-98-1, name is 1-(Pyrimidin-2-yl)piperidin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. name: 1-(Pyrimidin-2-yl)piperidin-4-ol

EXAMPLE 89: Preparation of (2R,3R)-2-(2,4-difluorophenyl)-3-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol To a solution of 1-(pyrimidin-2-yl)piperidin-4-ol (19.4 mg, 0.08 mmol) in N,N-dimethylformamide (0.5 mL) was added potassium tert-butoxide (10.7 mg, 0.01 mmol), followed by stirring at room temperature for 2 hrs. The resulting solution was mixed with 1-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole (20.0 mg, 0.08 mmol) and anhydrous calcium carbonate (13.2 mg, 0.01 mmol) and stirred at room temperature for one hr. The resulting reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous ammonium chloride solution and then with saline to separate an organic solvent layer. The organic solvent layer was dried over anhydrous magnesium sulfate and concentrated by evaporation at reduced pressure. The concentrate was purified using silica gel chromatography to afford the title compound (yield 21 %).1H-NMR(CDCl3, 300 MHz) delta 8.30(d, 1H, J=1.4Hz), 8.28(d, 1H, J=2.6Hz), 7.87(s, 1H), 7.62(s, 1H), 7.37(d, 1H, J=1.2Hz), 7.22-7.13(m, 1H), 6.99-6.86(m, 2H), 5.38(s, 1H), 4.45-4.28(m, 2H), 3.99-3.91(m, 1H), 3.35-3.26(m, 2H), 2.00-1.92(m, 2H), 1.59-1.47(m, 2H), 1.33-1.31(dd, 3H, J=3.1Hz, J=3.4Hz).

With the rapid development of chemical substances, we look forward to future research findings about 893755-98-1.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; PARK, Joon Seok; YU, Kyung A; YOON, Yun Soo; HAN, Mi Ryeong; KIM, Ji Duck; WO2011/99804; (2011); A2;,
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Pyrimidine – Wikipedia

Synthetic Route of 26305-13-5, 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. 26305-13-5, name is 2,4-Dihydroxy-5,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below.

2,4-Dichloro-5,6-dimethylpyrimidine (RJ1-008) (WO2013/123401): A mixture of RJ1-006 (4.00 g, 28.5 mmol), phosphorus(V) oxychloride (60 mL, 0.642 mol), and dimethylformamide (0.08 mL, 1.03 mmol) was heated to reflux at 110 C for 23 hours. The reaction mixture was then cooled to ambient temperature and evaporated. Toluene (80 mL) was added to the residue and the resulting mixture was concentrated. Cold water with ice (160 mL) was added to the residue, and the mixture was extracted with chloroform (3 x 60 mL). The combined organic layers were washed with brine (2 x 150 mL), dried over sodium sulfate, filtered, and concentrated to provide RJ1-008 as a pale yellow solid (4.37 g, 87%). m.p. = 68-70 C. XH NMR (400 MHz, CDCb) delta 2.55 (s, 3H), 2.34 (s, 3H). LRMS (ESI+) m/z 177.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26305-13-5, 2,4-Dihydroxy-5,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 13627-49-1, name is 2-Methylpyrimidine-4-carboxylic acid, molecular formula is C6H6N2O2, 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. SDS of cas: 13627-49-1

Example 76cis 2-Methyl-pyrimidine-4-carboxylic acid [2-(3,5-difluoro-phenyl)-1-oxo-2-aza-spiro[4.5]dec-7-yl]-amide Example 76 was also prepared from intermediate 33 via the process of Scheme 1, supra, as follows:In a round-bottom flask was charged with cis-7-amino-2-(3,5-difluoro-phenyl)-2-aza-spiro[4.5]decan-1-one. HCl (10.8 g, 34.1 mmol), 2-methylpyrimidine-4-carboxylic acid (4.71 g, 34.1 mmol), and BOP (15.1 g, 34.1 mmol). Methylene chloride (218 mL) was added, and the mixture was cooled at 0 C. Triethylamine (14.2 mL, 102 mmol) was added dropwise. The mixture was warmed up to rt and stirred at rt overnight. The mixture was diluted with methylene chloride (100 mL) and water (50 mL). The aqueous layer was extracted with CH2Cl2 (100 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue obtained was crystallized from ethyl acetate to afford 8.8 g (77%) of the title compound cis 2-Methyl-pyrimidine-4-carboxylic acid [2-(3,5-difluoro-phenyl)-1-oxo-2-aza-spiro[4.5]dec-7-yl]-amide: 1H NMR (400 MHz, CDCl3): delta8.85 (d, J=5.0 Hz, 1H), 8.10 (d, J=8.1 Hz, 1H), 7.89 (d, J=5.4 Hz, 1H), 7.28-7.35 (m, 2H), 6.60 (tt, J=8.8, 2.5 Hz, 1H), 4.07-4.18 (m, 1H), 3.74-3.80 (m, 2H), 2.79 (s, 3H), 2.07-2.28 (m, 3H), 1.89-1.97 (m, 2H), 1.55-1.85 (m, 4H), 1.37-1.48 (m, 1H). ESI-MS m/z: 401 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 13627-49-1.

Reference:
Patent; H. LUNDBECK A/S; US2011/98299; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3289-50-7 ,Some common heterocyclic compound, 3289-50-7, molecular formula is C6H9N3O2, 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 1 N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-2-methylbenzenesulfonamide To a stirred mixture of 2.40 g of 4-amino-2,6-dimethoxypyrimidine in 40 ml methylene chloride at ambient temperature and pressure was slowly added 3.0 g of 2-methylbenzenesulfonylisocyanate. The reaction was stirred 40 minutes, filtered, and the solid thereby obtained was washed with a small amount of acetonitrile; yield 4.0 g, m.p. 174-175, NMR (DMSO-d6) relative to tetramethylsilane: delta 2.77, S, area 30; delta 4.05, S, area 60; delta 6.85, S, area 89; delta 7.7-8.6, multiplets, area 45; delta 10.00, S, area 9.

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. 3289-50-7, 4-Amino-2,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4221585; (1980); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5466-43-3, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, 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, 5466-43-3, blongs to pyrimidines compound. Recommanded Product: 5466-43-3

To a stirred solution of 2,4-dichioro-6,7-dihydro-5H- cyclopenta[dlpyrimidine (600 mg, 3.17 mmoi) in i-PrOH (50 mL) were added TEA (963 mg, 9.52 mmol) and 3-4arninomethyi)phenoi (469 mg, 3.8() mmol).The mixture was stirred at 110C under N2 atmosphere for 15 hrs, cooled to it,concentrated and purified on silica gel column (hexane/ethyl acetate) to affbrd3 -(((2chioro-6,7-dihydro5Hcyciopenta[dipvriniidin-4-yI)arnino)methyI)phenoi(370 mg, 38%) as a white solid LCMS (M-F-W) ith: Calcd: 276.1; Found:276.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Patent; CLEAVE BIOSCIENCES, INC.; ZHOU, Han-Jie; WUSTROW, David; (498 pag.)WO2016/200840; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 57489-77-7, 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.57489-77-7, name is 5,7-Dichloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H3Cl2N3, molecular weight is 188.01, as common compound, the synthetic route is as follows.

Step C – Synthesis of 5-chloropyrazolo[ 1 ,5-a]pyrimidin-7-amine (Int-9c)To 5,7-dichloropyrazolo[ 1 ,5-a]pyrimidine (Int-9b, 7.6 g, 40.4 mmol) in a sealed vessel was added NH4OH (100 mL). The vessel was then sealed and heated at 85 0C for 2.5 hours, at which time the consistency of the white solid had changed (from foamy white solid to free-flowing white solid). The vessel was removed from the heat source and allowed to cool to room temperature overnight. On cooling, the contents of the vessel were collected and dried by vacuum filtration giving 5-chloropyrazolo[l,5- a]pyrimidin-7-amine (Int-9c) as a yellow-tinged white solid (6.8 g, 40.3 mmol, 100%).

The chemical industry reduces the impact on the environment during synthesis 57489-77-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; CHENG, Cliff, C.; ZENG, Hongbo; SHIPPS, Jr., Gerald, W.; DENG, Yongqi; MENG, Zhaoyang; ZHAO, Lianyun; NAN, Yang; SUN, Binyuan; LIU, Duan; REDDY, Panduranga, A.; SIDDIQUI, M., Arshad; WO2011/2887; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 90905-33-2 ,Some common heterocyclic compound, 90905-33-2, molecular formula is C6H6N2O, 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 4-6 (5.5 g, 16.2 mmol), 5-formyl-2-methylpyrimidine (4-6a, 1.8g, 14.7 mmol; for preparation, see J. Heterocyclic Chem., 28, 1281 (1991)) in 40 mL DMF wasadded K2C03 (4.07 g, 32 mmol). The mixture was stirred at ambient temperature for 15 hr, and concentrated to a paste. The residue was diluted with water, extracted with ethyl acetate, and dried over magnesium sulfate. Following concentration, the residue was chromatographed on silica gel (70 chloroform / 25 ethyl acetate / 5 methanol) to give 4-7 as a white solid. Rf= 0.20 (silica, 70 chloroform / 20 ethyl acetate / 10 methanol).?H NIVIR (400 MFIz, CDC13) oe 8. 80(s, 2H), 7.44 (d, 1H, J16Hz), 7.05 (d, 1H, J=7Hz), 6.81 (d,1H, J16Hz), 6.35 (d, 1H, J=7Hz), 4.72 (br s, 1H), 3.39 (m, 2H), 2.69 (s, 3H), 2.64 (m, 4H), 2.58(m, 2H), 1.91 (m, 2H), 1.74 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90905-33-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Jason, M.; MA, Lijun; ZHOU, Xiaoyan; HAIMBACH, Robin, E.; COLEMAN, Paul, J.; ZHOU, Haihong; KELLEY, David, E.; STOCH, Selwyn Aubrey; DUONG, Le, T.; HOEK, Maarten; (68 pag.)WO2016/154369; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3438-48-0 ,Some common heterocyclic compound, 3438-48-0, molecular formula is C10H8N2, 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.

The intermediate b (10 g, 0.06 mol)Was added to 500 mL of formamide,Stirred at room temperature for 30-60 minutes,After the intermediate b was completely dissolved,Transferred to the cold wells, the temperature control in 10 below,Dropping 20mL of concentrated sulfuric acid,While dropping hydrogen peroxide (50 mL)And aqueous ferrous sulfate heptahydrate solution (100 mL)Drop complete, 10-15 reaction 30min,After the reaction was completed, 2000 mL of water was added,Saturated sodium carbonate aqueous solution adjusted to pH 9,Dichloromethane was extracted three times (200 mL * 3)The combined dichloromethane was washed once with saturated brine,Dry methylene chloride as a white solid 5.7 g, yield 48%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-48-0, its application will become more common.

Reference:
Patent; Shenyang Pharmaceutical University; Gong, Ping; Zhao, Yanfang; Liu, Yaijing; Di, Xin; Tang, Qidong; (42 pag.)CN104072480; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 59989-18-3, 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. 59989-18-3, name is 5-Ethynylpyrimidine-2,4(1H,3H)-dione, molecular formula is C6H4N2O2, 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.

Under argon, cuprous iodide (0.02 mmol, 3.8 mg) and tetraphenylphosphine were used Palladium (0.02 mmol, 23 mg) and 1-octane, 5-ethynyluracil. 4 mmol, 99.6 mg) were added successively to a solution of 4,4-dodecylalkynyl-2,6- (0.2 mmol, 225.8 mg). Triethylamine (5 mL) was injected into the above mixture with a syringe and incubated in an oil bath at 60 C In response to four hours. Thin layer chromatography, until the reaction is complete, the reaction is also added 20mL water quenching reaction. The product was extracted with ether (3 x 40 mL) and the organic phase was washed three times with water (3 x 40 mL). Anhydrous magnesium sulfate drying, vacuum distillation solvent. The crude product was separated and purified by column chromatography, and the eluent was dichloromethane: ethyl acetate = 10: 1, volume ratio. The product was recrystallized from n-pentane as a purple-red solid, 199 mg in 60% yield.

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 59989-18-3, 5-Ethynylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Tianjin University; Chen Zhijian; Liu Ping; (17 pag.)CN107056829; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia