Day: February 26, 2021

Reference of 6693-08-9, 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 6693-08-9, name is 2,4,6-Trichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-amino-5-isoproxypyrazole (1.75 g, 12.41 mmol) in THF (20 ml) was added triethylamine (1.51 g, 14.89 mmol) and then slowly a solution of 2,4,6-trichloro-5- fluoropyrimidine (WO200549033, 2.50 g, 12.41 mmol) in THF (20 ml) at 0 0C. The resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was diluted with EtOAc. The solution was then washed with brine twice. The organic layer was obtained and evaporated to dryness. The dried residue was subject to silica gel chromatographic purification (by ISCO Combiflash with gradient EtOAc/hexanes) to afford EPO the desired product (1.40 g, yield 79%). LC-MS, 264 (M-41); 1H NMR (CDCl3) delta 8.70 (s, IH), 5.90 (s, IH), 4.50 (m, IH), 1.22 (d, 6H).

According to the analysis of related databases, 6693-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/123113; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 35265-82-8, 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 35265-82-8, name is 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

At normal temperature a solution of bromine (1.44 mE, 27.6 mmol) in acetic acid (10 mE) was slowly added dropwise into a solution of 8-g (prepared according to the method ofpatent: W02007/023382A2)(1.984 g, 9.2mmol) and aluminum trichloride (2.46 g, 18.4 mmol) in acetic acid (30 mE). The mixture was heated to 80 C. to react for 6 irs afier the addition was completed. The reaction mixture was cooled, and then partitioned between ethyl acetate (80 mE) and water (80 mE). The organic layer was separated and washed with 5% sodium thiosulfate solution (2×80 mE). The aqueous phase was extracted with ethyl acetate (x2), the combined organic phase was washed sequentially with saturated sodium bicarbonate solution (200 mE) and saturatedbrine (400 mE), dried over anhydrous sodium sulfate, and concentrated under reduced pressure, to yield target compound 8-f(1 .035 g, yield 76%) as a pale yellow solid. EC-MS (ESI): mlz 296.9 (M+H).

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 35265-82-8, 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine.

Reference:
Patent; SHANGHAI YINGLI PHARMACEUTICAL CO., LTD; XU, Zusheng; (174 pag.)US2016/214994; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 65996-50-1, 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 65996-50-1 as follows.

(4) To 1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione (35.0g) was added aqueous 1N sodium hydroxide solution (231ml) and after stirring for a while, the mixture was concentrated in vacuo. The residue was subjected to azeotropic distillation with toluene. To the residue was gradually added phenylphosphonic dichloride (239g) and then the temperature of the mixture was raised to 180C, followed by stirring for 3 hours. Thereto was further gradually added phenylphosphoric dichloride (100g) and the mixture was stirred overnight. The reaction mixture was gradually poured into ice-water under stirring and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate solution, dried and concentrated in vacuo. To the residue was added ethyl acetate/ diisopropyl ether to give 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine as crystals (19.96g). APCI-MS (m/e): 188/190 (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,65996-50-1, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP1956009; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1152107-25-9, Adding some certain compound to certain chemical reactions, such as: 1152107-25-9, name is Gsk-1322322,molecular formula is C22H34FN7O4, 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 1152107-25-9.

Example 10 Synthesis of N-(( ?)-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)- hexahydro pyrazino[2,1 -c][1,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4- yl)hydrazinyl)-3-oxopropyl)-N-hydroxyformamide methanesulfonateN-(( ?)-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)-hexahydropyrazino[2,1- c][1,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4-yl)hydrazinyl)-3-oxopropyl)-N- hydroxyformamide methanesulfonateTo a 1-L Labmax was added N-(( )-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)- hexahydropyrazino[2, 1-c][1 ,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4-yl)hydrazinyl)-3- oxopropyl)-N-hydroxyformamide (100 g, 209 mmol) and n-Propanol (600 mL). The contents were heated to 60C and methanesulfonic acid (13.54 mL, 209 mmol) was added via pipette. Solution was transferred through filter paper and into a clean 1-L Labmax. A rinse of n-propanol (100 mL) was transferred through the filter and into the clean 1-L Labmax. The resulting solution was adjusted to 50C. The solution was seeded with N-((f?)-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)-hexahydropyrazino[2, 1- c][1 ,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4-yl)hydrazinyl)-3-oxopropyl)-N- hydroxyformamide methanesulfonate Form 1 (1.0 g, 1.7 mmol). The resulting slurry was aged for 1 hour at 50C. The slurry was cooled to 20C at a linear rate of0.1 C/min. The slurry was aged for 2 hours at 20C. The slurry was cooled to 0C at a linear rate of 0.1 C/min and aged overnight. The slurry was filtered under nitrogen and the cake was washed with chilled n-propanol (100 mL). The resulting wet cake was blown with nitrogen. The wet cake was then dried under vacuum at 50C. After drying, 104 g (86.7% yield) of N-(( )-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)- hexahydropyrazino[2, 1-c][1 ,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4-yl)hydrazinyl)-3- oxopropyl)-N-hydroxyformamide methanesulfonate was obtained. H NMR (500 MHz, DMSO-d6, referenced to TMS = 0.00 ppm, T = 25 C, rotamers present due to hindered rotation, major rotamers listed with integration rounded to nearest 1/2 units) delta ppm 10.5-9.7 (3H, several broad s), 9.05 (1/2 H, s), 9.02 (1/2 H, s), 8.31 (1/2 H, s), 7.87 (1/2 H, s), 4.38 (1 H, d, J = 13 Hz), 4.30 (1 H, d, J = 14 Hz), 4.08-4.00 (2H, several m), 3.80-3.72 (3/2 H, several m), 3.56-3.24 (17/2 H, several m), 3.02-2.98 (1 H, m), 2.82-2.69 (1 H, several m), 2.38 (3H, s), 2.26-2.23 (3H, several s), 1.99-1.90 (2H, several m), 1.71 (1 H, broad m), 1.66-1.47, (5H, several m), 1.27- 1.20 (1 H, m), 1.08-1.02 (2H, several m).3C NMR (126 MHz, DMSO-d6, referenced to DMSO-d6 = 39.51 ppm, T = 25 C, rotamers present due to hindered rotation, major rotamers listed with integration rounded to nearest 1/2 units) delta ppm 172.8 (rotamer 1/2 C), 172.7 (rotamer 1/2 C), 162.0 (rotamer 1/2 C), 160.1 (d, J13C-I9F = 9 Hz) (rotamer 1/2 C), 160.0 (d, J13C-I9F = 9 Hz) (rotamer 1/2 C), 157.4 (rotamer 1/2 C), 152.5 (d, J13C-I9F = 10 Hz), 148.2 (broad), 130.4 (d, J13C-19F = 249 Hz) (rotamer 1/2 C), 130.3 (d, J13C-I9F = 249 Hz) (rotamer 1/2 C), 65.2, 63.7, 60.1 , 52.0 (rotamer 1/2 C), 51.7, 51.4, 48.9 (rotamer 1/2 C), 43.8 (broad), 43.4 (broad), 41.2 (rotamer 1/2 C), 41.1 (rotamer 1/2 C), 39.8, 37.0 (rotamer 1/2 C), 36.9 (rotamer 1/2 C), 35.6 (rotamer 1/2 C), 35.5 (rotamer 1/2 C), 32.9, 31.6, 24.9, 24.7 (2C).HRMS (ESI): calcd for C22H35FN704[M + H]+ 480.2730, found 480.2731.

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. 1152107-25-9, Gsk-1322322, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY NO 2 LIMITED; BULLOCK, Kae Miyake; DESCHAMPS, Nicole; ELITZIN, Vassil; FITZGERALD, Russell; GRADDY, William Hawthorne; MATSUOKA, Richard Tadao; MCKEOWN, Robert Rahn; MITCHELL, Mark Bryan; SHARP, Matthew Jude; SUTTON, Peter W.; TABET, Elie Amine; ZHOU, Xiaoming; WO2014/141181; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 111196-81-7, Adding some certain compound to certain chemical reactions, such as: 111196-81-7, name is 2-Chloro-5-ethylpyrimidine,molecular formula is C6H7ClN2, 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 111196-81-7.

To a reaction flask was added compound18(700 mg, 2.19 mmol) and 2-chloro-5-ethylpyrimidine (621 mg, 4.37 mmol) in one-portion in the presence of anhydrous DMF. After stirring at room temperature for 5 min, to the resulting clear solution was added anhydrous K2CO3(453 mg, 3.28 mmol) in one-portion. The reaction flask immersed in a pre-heated oil-bath (90) and the reaction mixture was stirred at 90for 4 h and cooled to room temperature. To the reaction mixture at room temperature under vigorous stirring and H2O was added slowly dropwise over 30 min to give an off-white slurry. After the addition was finished, the resulting slurry was stirred at room temperature for additional 10 min. The precipitate was filtered and then rinsed with H2O (2 x 30 mL) and the precipitate was dissolved in EtOAc, and washed with H2O (2 x 30 mL). The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purifiedby silica gel column chromatography using 40% EtOAc in hexanes to afford compound19(680 mg, 73%).1H-NMR (CDCl3, 300 MHz) delta 9.87 (1H, s, CHO), 8.19 (2H, s, pyrimidine), 7.64 (2H, d,J= 6.9 Hz, Ar), 7.29 (1H, s, thiazole), 7.18 (1H, t,J= 6.9 Hz, Ar), 5.32 (2H, s, OCH2), 4.81 (2H, d,J= 6.0 Hz, CH2), 3.33 (1H, t,J= 12.3 Hz, CH), 3.25 (2H, t,J= 9.3 Hz, CH2), 2.46 (2H, q,J= 9.3 Hz, CH2), 2.19 (2H, d,J= 11.7 Hz, CH2), 1.79 (2H, dq,J= 12.0 Hz, 2.7 Hz, CH2), 1.22 (3H, t,J= 9.0 Hz, CH3).

According to the analysis of related databases, 111196-81-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Hyojin; Cho, Suk Joon; Yoo, Minjin; Kang, Seung Kyu; Kim, Kwang Rok; Lee, Hwan Hee; Song, Jin Sook; Rhee, Sang Dal; Jung, Won Hoon; Ahn, Jin Hee; Jung, Jae-Kyung; Jung, Kwan-Young; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5213 – 5220;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 799842-07-2 , The common heterocyclic compound, 799842-07-2, name is N-[5-Bromomethyl-4-(4-fluorophenyl)-6-isopropylpyrimidine-2-yl]-N-methylmethane sulfonamide, molecular formula is C16H19BrFN3O2S, 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-3Preparation of N-[4-(4-FIuoro-phenyl)-6-isopropyI-5-(pyridin-2-ylsulfanylmethyl)- pyrimidin-2-yI]-N-methyl-methanesulfonamide (III)2-mercaptopyridine (II) 3.23g was taken in 16mL tetrahydrofuran and chilled to -25 to -30 C and added 30% n-butyl lithium(l 1.OmL) drop wise at -5 to -10 C and stirred at the same temperature for one hour. Added N-[5-Bromomethyl-4-(4-fluoro-phenyl)-6- isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (11. Og) dissolved in 22 mL THF at -60 C to -700C drop wise and stirred for 15 minutes at -60 to-70 C. Slowly brought the temperature to 250C and stirred for 2 h. Adjusted the pH of the reaction mixture to 7-8 with saturated ammonium chloride and added 5OmL ethyl acetate and separated the layers. Organic layer was given water washes and a brine wash. Organic layer was dried over anhydrous sodium sulphate and concentrated to get solid N-[4-(4- Fluoro-phenyl)-6-isopropyl-5-(pyridin-2-ylsulfanylmethyl)-pyrimidin-2-yl]-N-methyl- methanesulfonamide (V) Yield: 11. Og

The synthetic route of 799842-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCON LIMITED; ANEGONDI, Sreenivasa, Prasad; RAJMAHENDRA, Shanmughasamy; JOSEPH, Jibin; SRINIVAS, Pullela, Venkata; WO2010/23678; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 87253-62-1, 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 87253-62-1 as follows.

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,87253-62-1, its application will become more common.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
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 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 287714-35-6

To the reaction mixture of methyl 2-chloropyrimidine-5-carboxylate (2.5 g, 14.487 mmol) in THE (10 mL), methyl magnesium chloride (14.487 mL, 43.463 mmol) was added drop wise at 0C and the mixture was stirred at rt for 30 mm. After completion of reaction the reaction mixture was poured into 50 mL of IN HCI and extracted with ether. The ether layer was washed with water, dried over anhydrous Na2SO4 and concentrated. The resulting crudeproduct was purified by flash chromatography (Elutant: 55-60% EtOAc in pet ether) to afford title compound (pale yellow solid). 1H NMR (400 MHz, DMSO-d6): 6 1.48 (5, 6H), 5.51 (5, IH), 8.84 (5, 2H). LCMS: (Method A) 173.0 (M +H), Rt. 1.659 mm, 98.64% (Max).

With the rapid development of chemical substances, we look forward to future research findings about 287714-35-6.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (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 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. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C11H15ClN2O2

Step A 9-((tert-butyldimethylsilyl)oxy)-3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one A solution of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (1.0 g, 4.12 mmol) in DMF (5 mL) was treated with 1H-imidazole (701.24 mg, 64.66 mmol), followed by a solution of t-butyldimethylchlorosilane (683.12 mg, 4.53 mmol) in DMF (1 mL). After stirring for 18 h at room temperature, the solvents were removed under vacuum and the residue was taken up in dichloromethane/water (10 mL/10 mL) with addition of a spatula of potassium carbonate. The aqueous layer was extracted with dichloromethane (three times 10 mL). The combined organic fractions were dried over Na2SO4, filtered, and the solvent was removed under vacuum. The crude mixture was used without further purification in the next step. (ESI-MS (M+1) 357).

With the rapid development of chemical substances, we look forward to future research findings about 130049-82-0.

Reference:
Patent; Hryhorenko, Eric; Sankaran, Banumathi; DeCory, Thomas R.; Tubbs, Theresa; Colt, Linda; Vliegen, Maarten; Haspeslagh, Pieter Rik; US2014/57301; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5604-46-6, 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.5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, molecular formula is C5H3Cl2N3O, molecular weight is 192.0028, as common compound, the synthetic route is as follows.

A solution of methyl 1-hydrazinyl-1, 2, 3, 4-tetrahydronaphthalene-1-carboxylate hydrochloride (0.7 g, 2.7 mmol) and 2-amino-4, 6-dichloropyrimidine-5-carbaldehyde (0.52 g, 2.7 mmol) in MeCN (30 ml) was stirred at rt overnight and then heated to 70. The reaction mixture was stirred at 70 for 1h. After completion, the mixture was filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography with PE: EtOAc (5: 1) to afford product (0.66 g, 68%) as a light yellow solid. MS: M/e 358 (M+1) +.

The chemical industry reduces the impact on the environment during synthesis 5604-46-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia