Day: March 4, 2021

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 1100318-96-4, name is 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

306) To a solution of 4-iodo-7H-pyrrolo[2,3-d]pyrimidine (2784.4 mg, 11.36 mmol) in dry THF (30.0 mL) was added pyridine (0,92 mL, 1 1.34 mmol), DIAD (4,7 mL, 23.82 mmol), tributylphosphane (5.7 mL, 22.68 mmol) and [(R)-(4-chlorophenyl)-[(2S,3S,4R)-3,4,5- trihydroxytetrahydrofuran -2-yl] methyl] 4-phenylbenzoate (Int-2-3) (5000.0 mg, 11.34 mmol) under N2. The reaction mixture was stirred at 30 C for 1 h under N2. LCMS showed the reaction was completed. The mixture was purified by silica chromatography column (DCM : CH OH = 100 : 1 to 60 : 1) to give [(R)-(4-chlorophenyl)-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(4-iodopyrrolo[2,3- d]pyrimidin-7-yl)tetrahydrofuran-2-yl]methyl] 4-phenylbenzoate (104a) (2.0 g, 2.99 mmol, 26.4% yield). LCMS [M+H] : 668.2.

With the rapid development of chemical substances, we look forward to future research findings about 1100318-96-4.

Reference:
Patent; PRELUDE THERAPEUTICS, INCORPORATED; LUENGO, Juan; LIN, Hong; (0 pag.)WO2018/160855; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 16019-33-3, 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. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, molecular formula is C6H4Cl2N2O, 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.

(4,6-Dichloro-pyrimidin-5-yl)-acetadehyde (1.26 g, 6.37 mmol) was added to a solution of ci33-(1 ,1 -dioxo-1 -thiomorpholin-4-ylmethyl)-cyclobutylamine (Step N.3, 1 .21 g, 5.54 mmol) in diisopropylethylamine (1.98 ml 1 1.1 mmol) and ethanol (28 ml) at room temperature and the reaction mixture was then heated for 5 hours at reflux. After cooling to room temperature the reaction mixture was diluted with ethyl acetate, washed with aqueous sodium bicarbonate, then saturated brine, dried over sodium sulphate and evaporated. Purification by flash column chromatography, eluting with a gradient of methanol in DCM, gave the title compound. HPLC/MS tR 0.89 min, M+H 355.4 (Method X).

According to the analysis of related databases, 16019-33-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; IRM LLC; CHEN, Bai; FAIRHURST, Robin Alec; JIANG, Songchun; LU, Wenshuo; MARSILJE III, Thomas H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STUTZ, Stefan; WO2012/120469; (2012); 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. 956034-07-4, name is 2,4-Dichlorofuro[3,2-d]pyrimidine, molecular formula is C6H2Cl2N2O, 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. Quality Control of 2,4-Dichlorofuro[3,2-d]pyrimidine

Step A: 2-Chloro-/V-(2,2-difluoroethyl)furo[3,2-i/|pyrimidin-4-amineTo a flask was added 2,4-dichlorofuro[3,2-i/]pyrimidine (2 g, 10.58 mmol, Arkpharm), DCM (20 mL) and TEA (2.95 mL, 21.16 mmol). A solution of 2,2-difluoroethanamine (0.858 g, 10.6 mmol, Matrix) in DCM (5 mL) was added drop-wise and the mixture was stirred at rt overnight. The mixture was concentrated under reduced pressure. To the residue was added 1,4-dioxane (20 mL), TEA (2.95 mL, 21.2 mmol) and a solution of 2,2-difluoroethanamine (0.858 g, 10.58 mmol, Matrix) in 1,4-dioxane (5 mL). The mixture was stirred at rt for about 4 h, and then at about about 55 C overnight. The mixture was concentrated under reduced pressure, and the residue was taken up in EtOAc (120 mL) and water (25 mL). The organic layer was isolated and washed with water (2 x 25 mL). The combined aqueous layers were washed with EtOAc (2 x 25 mL). The combined organic layers were washed with brine (25 mL), dried with MgS04, filtered, concentrated under reduced pressure, and dried in a vacuum oven at about 70 C over 2 days to give 2-chloro-^-(2,2-difluoroethyl)furo[3,2-i/]pyrimidin-4-amine (2.20 g, 89 %): LC/MS (Table 2, Method c) R, = 1.69 min.; MS m/z: 234 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 956034-07-4.

Reference:
Patent; ABBOTT LABORATORIES; CALDERWOOD, David, J.; WILSON, Noel, S.; COX, Philip; HOEMANN, Michael, Z.; CLAPHAM, Bruce; MULLEN, Kelly, D.; VASUDEVAN, Anil; VILLAMIL, Clara I; LI, Bin; SOMAL, Gagandeep; WO2012/48222; (2012); A1;,
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, Computed Properties of C7H6Cl2N2, blongs to pyrimidines compound. Computed Properties of C7H6Cl2N2

General procedure: To a solution of 2,4-dichloro-5-fluoroquinazoline (22a) (100.00mg, 460.77 mumol, 1.00 eq) in THF (3.00mL) was added methyl (2S,3S)-3-aminobicyclo[2.2.2]octane-2-carboxylate (84.44mg, 460.77 mumol, 1.00 eq) and DIPEA (238.20mg, 1.84mmol, 4.00 eq) at room temperature overnight. H2O (20mL) was added to the mixture and extracted with EtOAc (10mL¡Á3). The combined organic layers were dried over Na2SO4 and concentrated in vacuum. The residue was purified by column chromatography on silica gel with PE:EtOAc (10:1 to 5:1) to give compound 23a (130.00mg, 357.33 mumol, 77.55% yield) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5466-43-3, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Xiong, Jian; Wang, Jingjing; Hu, Guoping; Zhao, Weili; Li, Jianqi; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 249 – 265;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 131860-97-4, 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.131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, molecular weight is 320.73, as common compound, the synthetic route is as follows.

A slurry containing methyl (E)-I- {2-[6~chloropyrimidin-4-yloxy]phenyl} -3-methoxyacrylate (80.9g at 99%, 0.25mols), potassium carbonate (52.8g at 98%, 0.375mols) and 2- cyanophenol (33.6g at 97.5%, 0.275mols) in MIBK (16OmIs) was heated to approximately 6O0C. A solution of DABCO (0.28g, 0.0025mols) in MlBK (1 OmIs) was added. The mixture was heated to 8O0C and held at this temperature for 360 minutes. Water (30OmIs) was charged to the reaction, maintaining the temperature in the range 70-800C. The mixture was stirred for 70 minutes then settled and the lower aqueous phase separated. The MIBK solution (235.3g) contained methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4- yloxyjphenyl} -3-methoxyacrylate (41.0%w/w) 95.8% of theory.; c) Coupling of methyl rE)-2-{2-[6-chloropyrimidin-4-yloxylphenyl|-3-methoxyacrylate with 2-cvanophenol in MIBK with lmol% DABCO added after the 2-cyanophenol, that is, last. EPO A slurry containing methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (80.9g at 99%, 0.25mols), potassium carbonate (52.8g at 98%, 0.375mols) and 2- cyanophenol (33.6g at 97.5%, 0.275mols) in MIBK (16OmIs) was heated to approximately 6O0C. A solution of DABCO (0.28g, 0.0025mols) in MBK (1 OmIs) was added. The mixture was heated to 8O0C and held at this temperature for 240 minutes (residual (¡ê)-2- {2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate at the end of reaction was 4.4% by area on GC). Water (30OmIs), at 6O0C, was charged to the reaction, maintaining the temperature in the range 70-800C. The mixture was stirred for 40 minutes then settled and the lower aqueous phase separated. The MIBK solution (237.Ig) contained methyl (E)-2-{2-[6-(2- ” cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (38.7%w/w) 89.1% of theory.

Statistics shows that 131860-97-4 is playing an increasingly important role. we look forward to future research findings about (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; SYNGENTA LIMITED; WO2006/114572; (2006); A2;,
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. 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C17H13N5O, 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. HPLC of Formula: C17H13N5O

a) 4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]benzaldehyde 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.0 g, 6.59 mmol) was mixed with 4-fluorobenzaldehyde (1.06 mL, 9.89 mmol), cesium carbonate (4.30 g, 13.19 mmol) in DMF (6 mL). The reaction mixture was heated at 86 C. overnight. After cooling to room temperature, the reaction mixture was poured onto ice water. The solid was collected by filtration to give 4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]benzaldehyde (2.46 g, 92%). 1H NMR (CDCl3) delta 7.19 (m, 5H), 7.46 (m, 2H), 7.78 (d, J=8.64 Hz, 2H), 8.10 (d, J=8.70 Hz, 2H), 8.44 (s, 1H), 8.59 (d, J=8.70 Hz, 2H), 10.03 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 330786-24-8.

Reference:
Patent; Abbott Laboratories; US6921763; (2005); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)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, 153435-63-3, blongs to pyrimidines compound. Quality Control of 2-(Tributylstannyl)pyrimidine

Intermediate 3 (75mg;1 eq) was dissolved in dry DMF (2ml), then CsF (49mg;2 eq), Cul (6mg;0.2 eq), [Ph3P]4Pd (19mg; 0.1 eq) and 2- pyrimidyltributylstannane(90mg;1 .5 eq; prepared according to Eur. J. Org. Chem. 2003, 171 1 -1721 ) were added. The mixture was warmed at 130C for 25 minutes (microwave), then poured in aqueous saturated solution of NH4CI and extracted with DCM. The organic layers were combined, washed with water, dried (Na2SO4) and concentrated under vacuum; crude product was purified by silica gel column chromatography (Cyclohexane/AcOEt 9/1 to AcOEt) then by SCX cartridge (5g) to obtain 13mg of the title compound.MS (ESI) m/z 468-470 ;1 HNMR (CDCI3) delta ppm 8.80-8.94 (m, 1 H), 8.66 (d, 1 H), 8.22-8.43(m, 1 H), 7.86- 8.07 (m, 1 H), 7.12-7.52(m, 4H), 6.22-6.74(m, 1 H), 4.98-5.22(m, 1 H),4.32-4.81 (m, 1 H), 3.08-3.97(m, 4H), 1 .90-2.40(m, 2H), 0.65-1 .65 (m, 2H), 0.15-0.65 (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,153435-63-3, its application will become more common.

Reference:
Patent; ROTTAPHARM S.P.A.; STASI, Luigi Piero; ROVATI, Lucio; WO2012/104338; (2012); 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. 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate, the common compound, a new synthetic route is introduced below. category: pyrimidines

To a solution of compound 4 (2.29 g 10 mmol) in dioxane (50 ml) was added compound 5 (1.87 g, 1.0 equiv.) and DIPEA (2.58 g, 2.0 equiv.). The mixture was heated overnight at 110-120 ¡ãC. The resulting mixture was directly purified on silica gel column to afford the coupled product, compound 6, as a white solid (1.37 g, 40percent)

The synthetic route of 89793-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; JONES, Simon, S.; QUAYLE, Steven, N.; SAHAKIAN, Eva; IBARZ, Javier, Pinilla; (83 pag.)WO2017/184774; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7226-23-5 ,Some common heterocyclic compound, 7226-23-5, molecular formula is C6H12N2O, 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 diisopropylamine (3.4 mL, 24.38 mmol) in dry tetrahydrofuran (21 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7 mL) was cooled to -78 C. under nitrogen and then treated with a 2.5M solution of n-butyllithium in hexanes (9.8 mL, 24.38 mmol). The resulting reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of (3-bromo-4-methylsulfanyl-phenyl)-acetic acid methyl ester (6.10 g, 22.17 mmol) in dry tetrahydrofuran (21 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7 mL). The resulting reaction mixture was allowed to stir at -78 C. for 1 h, at which time, a solution of iodomethylcyclopentane (5.59 g, 26.60 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm to 25 C. where it was stirred for 15 h. The reaction mixture was quenched with water (300 mL) and then concentrated in vacuo to remove tetrahydrofuran. The remaining aqueous phase was extracted with ethyl acetate (3*150 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1*200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 19/1 hexanes/ethyl acetate) afforded 2-(3-bromo-4-methylsulfanyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (4.52 g, 57%) as a light yellow oil: EI-HRMS m/e calcd for C16H21BrO2S (M+) 356.0446, found 356.0435.

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. 7226-23-5, 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bizzarro, Fred Thomas; Corbett, Wendy Lea; Grippo, Joseph Francis; Haynes, Nancy-Ellen; Holland, George William; Kester, Robert Francis; Sarabu, Ramakanth; US2001/39344; (2001); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 7752-78-5, 5-Bromo-2-methylpyrimidine, 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, 7752-78-5, blongs to pyrimidines compound. SDS of cas: 7752-78-5

A stirred solution of 5-bromo-2-methylpyrimidine(A18, 0.5 g 2.8 mmol), ethyl 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)imidazo[l,2-a]pyridine-2- carboxylate(1-26, 1.55 g, 4.9 mmol) and sodium carbonate(0.612 g, 5.7 mmol) in dioxane : water(4:1) 15 mL was degassed with argon for 20 minutes. Then[I,G- Bis(diphenylphosphino)ferrocene]palladium(II) dichloride(0.126 g, 0.17 mmol) was added. The reaction mixture was heated at 90C for 16 h. After completion, reaction mixture quenched with water and extracted with 20% MeOH in DCM(3 times). The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude. This crude purified by combiflash using 3% MeOH in DCM as eluent. The desired fractions were concentrated under reduced pressure to offered ethyl 6-(2-methylpyrimidin-5-yl)imidazo[l,2-a]pyridine-2-carboxylate 1-28 as dark solid. Yield: 0.64 g(78%) LC-MS(ES) m/z = 283.3[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,7752-78-5, its application will become more common.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia