Day: March 15, 2021

Synthetic Route of 7752-82-1 ,Some common heterocyclic compound, 7752-82-1, molecular formula is C4H4BrN3, 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.

[00159] Scheme 1. Preparation of relevant pyri(mi)dyl halides A-H. Key: (a) NBS, NH4OAc, MeCN, rt, 5 min, pyr: 85-90%; pym: quant; (b) pyr: RCHO, Na(CN)BH3, MeCN, reflux, 1-12h (82%, R = C5Hn); pym: NaH, Rl, THF, rt, overnight (85%, R = Me); (c) Me3(Bn)NBr, f-BuONO, CH2Br2, rt, overnight, pyr: 77-83%; pym: 30- 40%; (d) pym: HI, CH2CI2, 0C, 80-85%; (e) i. NaOH, Br2, H20, rt, 50-60%, ii. POCI3, PhNEt2, reflux, 4h, 75-85%, iii. HI, CH2CI2, 0C, 80-85%; (f) ROH, Na, rt, 1-12 h, quant.; (g) RZnl, CI2Pd(PPh3)2, DMF/THF, rt, overnight, pyr (Br): 72% (R = C6H13), pym (I) 81 %, (R = C6H13); (h) alkyne, Cul, CI2Pd(PPh3)2, Et3N, MeCN, rt, 1-12 h, quant. [00161] The pyrimidyl bromides were prepared in a similar manner, beginning with bromination of 2-aminopyrimidine. N-Alkylation could not be achieved by reductive amination (presumably due to the decreased nucleophilicity of the amine) and was instead accomplished using NaH and an appropriate alkyl halide to give (B). Nonaqueous diazotization/halo-dediazoniation was used to prepare 5-bromo-2- halopyrimidines, but in diminished yield relative to the analogous reaction with the 2- aminopyridine (again, presumably due to the decreased nucleophilicity of the amine group). Alternatively, 2-pyrimidinone could serve as a precursor to 5-bromo-2- halopyrimidines (Lutz, F.; Kawasaki, T.; Soai, K. Tetrahedron-Asymmetry 2006, 17, 486.) or as a substrate for alkylation to generate 5-bromo-2-alkoxypyrimidines (D) (Kokatla, H. P.; Lakshman, M. K. Org. Lett. 2010, 12, 4478.) Introduction of an alkyne substituent at the 2-position to give ( proceeded satisfactorily under Sonogoshira conditions, but alkylation using Negishi conditions was unselective. Since reduction of the 2- alkynylpyrimidyl bromide (F) to the corresponding 2-alkyl pyrimidyl bromide (H) was complicated by competing removal of the bromine, we turned to 5-bromo-2- iodopyrimidine as a precursor for the cross coupling reactions and saw a dramatic improvement in selectivity and yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7752-82-1, its application will become more common.

Reference:
Patent; QUEEN’S UNIVERSITY AT KINGSTON; UNIVERSITA DI BOLOGNA; PRATT, Derek A.; HANTHORN, Jason, J.; VALGIMIGLI, Luca; WO2012/162818; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 120747-84-4, 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. 120747-84-4, name is 2-Aminopyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

Preparation 3: Step 2: To a mixture of 20 (166 mg, 1.35 [MMOL),] DMAP (17 mg, 0.14 [MMOL)] and Et3N (418 [LLI,] 3.00 [MMOL)] in THF (10 ml) was added (BOC) [20] (589 mg, 2.7 [MMOL).] The mixture was stirred at RT for 5 h, concentrated-dry loaded on silica gel and flash chromatographed (1-3% [ACETONE/CH2CI2)] to produce 21 (117 mg, 0.36 [MMOL] ; 27%) as a clear oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,120747-84-4, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2004/831; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4786-52-1, 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 4786-52-1 as follows.

Ethyl 4-hydroxypy?miotadiotane-5-carboxylate (380 mg, 2.26 mmol) was dissolved in THF (5 mL) and treated with thionyl chloride (1.65 ml, 22.6 mmol). The solution was heated to reflux for 4 h and then concentrated in vacuo, yielding 417 mg (99%) of the crude product This material was used without purification or characterization

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4786-52-1, its application will become more common.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/49681; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3680-69-1, 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 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1 Preparation of 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine The solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (6.08 g, 39.07 mmol) in CH2Cl2 (100 mL) was heated to 60 C. for for 30 min. A solution of NBS (5.40 g, 39.07 mmol) in CH2Cl2 (100 mL) was added slowly in portions to this mixture. The mixture was refluxed for an additional 50 min and allow to cool to rt. Filter off the off white solid and washed with water, dried in vacuum oven to give 7.7 g of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. MS (ESI) 234.5 (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 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Dillon, Michael Patrick; Bois, Daisy Joe Du; Lai, Yingjie; Hawley, Ronald Charles; Wang, Beihan; US2010/144758; (2010); 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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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. name: 4-Chloro-2-methylpyrimidine

A solution of 4-chloro-2-methylpyrimidine (100 mg, 0.778 mmol), hexamethylditin (129 mu, 0.622 mmol), tetrakis(triphenylphosphine)palladium (0) (44.9 mg, 0.039 mmol) and 6-bromo-3-fluoro-2-(fluoromethyl)pyridine (113 mg, 0.544 mmol) in 1,4-dioxane was purged with nitrogen and irradiated in a microwave at 120 C for 1 h. The reaction mixture was allowed to cool to room temperature and diluted with ethyl acetate (25 mL). The black suspension was filtered through diatomaceous earth (Celite) and the bed was washed with ethyl acetate (10 mL). The filtrate was concentrated under reduced pressure. The black residue was purified via silica gel chromatography (0-25% petroleum ether in ethyl acetate) to afford 4-(5- fluoro-6-(fluoromethyl)pyridin-2-yl)-2-methylpyrimidine (35 mg, 0.123 mmol, 16% yield) as a brown semi-solid. LCMS (ESI) m/e 222.9 [(M+H)+, calcd for (S)-2-amino-2,4-dimethylpentan-1-ol

With the rapid development of chemical substances, we look forward to future research findings about 4994-86-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 2915-16-4 ,Some common heterocyclic compound, 2915-16-4, molecular formula is C16H11ClN2, 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.

Preparation of Compound 13 [115] Compound 1-10 (2.7 g, 10.11 mmol), Compound 1-9 (5 g, 10.11 mmol), Pd(PPh3)4 (584 mg, 0.50 mmol), K2CO3(2M) (15 mL) and EtOH (15 mL) were dissolved in toluen (30 mL), and the mixture was heated at 120 . After the mixture was stirred for 3 hours, the reaction was completed. The reaction mixture was washed with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 13 (5 g, 72%) was obtained through purification by column chromatography.

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. 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; KIM, Hye Mi; KIM, Young Gil; CHO, Young Jun; KWON, Hyuck Joo; KIM, Bong Ok; KIM, Sung Min; WO2011/93609; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 63558-65-6, 4-Chloro-5-iodopyrimidine, 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, Quality Control of 4-Chloro-5-iodopyrimidine, blongs to pyrimidines compound. Quality Control of 4-Chloro-5-iodopyrimidine

Under nitrogen, a mixture of 4-chloro-5-iodopyrimidine (2.0 g, 8.32 mmol), 2- (methylthio)-4-(tributylstannyl)pyrimidine (3.8 g, 9.15 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.12 g, 1.60 mmol) in toluene (70 mL) was stirred for 16 h at 95 C. The reaction was quenched with a saturated solution of potassium fluoride. The mixture was extracted with ethyl acetate and washed with brine. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica flash chromatography (ethyl acetate/petroleum ether 20:80) to afford the title compound (534 mg, 26.9% yield) as a yellow solid. LCMS (ESI): [M+H]+ = 239.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63558-65-6, 4-Chloro-5-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; BRAUN, Marie-Gabrielle; GIBBONS, Paul; LEE, Wendy; LY, Cuong Q.; RUDOLPH, Joachim; SCHWARZ, Jacob Bradley; ASHKENAZI, Avi; BEVERIDGE, Ramsay; ZHAO, Liang; LEMIRE, Alexandre; FU, Leo; LAI, Kwong Wah; WANG, Fei; (100 pag.)WO2020/56061; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 672-41-3, 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. 672-41-3, name is 6-(Trifluoromethyl)pyrimidin-4-amine, molecular formula is C5H4F3N3, 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.

A solution of 6-(trifluoromethyl)pyrimidin-4-amine (0.14544 g, 0.89175 mmol) and 2-bromo-1-(5- bromo-3-ethylsulfonyl-2-pyridyl)ethanone (0.3 g, 0.81 mmol) in acetonitrile (9mL) were heated for 1 h at 150C in the microwave. After this time, the reaction mixture was evaporated. The solid obtained was dissolved in dichloromethane and washed with NaHC03 sat sol. The organic layer was then washed with brine, dried over Na2S04, filtered and concentrated in vacuo. Purification by Combi flash chromatography with a column of 12 g and a gradient of dichloromethane + 0-10% ethylacetate gave the title product as white powder. LCMS (method 1 ); Rt= 0.91 min, [M+H] 435/437. H NMR (400 MHz, chloroform-c/) delta ppm: 1 .40 (t, J=7.52 Hz, 3 H); 4.00 (q, J=7.46 Hz, 2 H); 7.97 (s, 1 H); 8.36 (s, 1 H); 8.69 (d, J=2.20 Hz, 1 H); 8.95 (d, J=2.20 Hz, 1 H); 9.17 (s, 1 H).

According to the analysis of related databases, 672-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; JEANGUENAT, Andre; JUNG, Pierre Joseph Marcel; MUEHLEBACH, Michel; (150 pag.)WO2016/71214; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1005-37-4, Adding some certain compound to certain chemical reactions, such as: 1005-37-4, name is 6-Chloro-N4-methylpyrimidine-2,4-diamine,molecular formula is C5H7ClN4, 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 1005-37-4.

Intermediate 41 -(3-aminophenyl)-4-N-methylpyrimidine-2,4-diamine. Tetrakis(triphenylphosphine)palladium (0) (5 mol%) was added to a stirred mixture of 6-chloro-4-N-methylpyrimidine-2,4-diamine (1.00 mmol), (3- aminophenyl)boronic acid (1.3 equiv.), sodium carbonate (3.2 equiv.), 1 ,4- dioxane (4 mL) and water (1 mL) in a tube. The tube was sealed and the reaction was heated at 90C for 5 h and then concentrated. The crude material was taken up in ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate, concentrated and purified by flash chromatography (0?15 % MeOH in DCM) to give the title compound. LCMS [M+H]+ 216.

According to the analysis of related databases, 1005-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
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.59549-51-8, name is 5-Bromo-2-chloro-4-(methylthio)pyrimidine, molecular formula is C5H4BrClN2S, molecular weight is 239.52, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-2-chloro-4-(methylthio)pyrimidine

A 3-L, 3-neck, round-bottom flask was equipped with a J-KEMtemperature controller, a mechanical stirrer, and a nitrogen inlet. The flask was charged with 5-bromo-2-chloro-4-(methylthio)pyrimidine (100 g, 417.5 mmol), (lr,4r)-4- aminocyclohexanol (76.4 g, 663.4 mmol), and ethanol (1 L). DIEA (109 mL,626.3 mmol) was added, and the mixture was heated to reflux overnight. TLC (1 : 1 hexanes/ethyl acetate) analysis after 20 h indicated complete reaction. The reaction was allowed to cool to room temperature. Water (300 mL) was added, and a precipitate gradually formed. The solid was filtered and washed with water to give 111.7 g of a white solid. The filtrate was extracted with ethyl acetate (3 x 300 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to a semi-solid. The semi-solid was slurried in 1 : 1 hexanes/ethyl acetate and filtered to give an additional 12.1 g of a white solid. The two batches were combined to give 123.8 g (93%) of (lr,4r)- 4-(5-bromo-4-(methylthio)pyrimidin-2-ylamino)cyclohexanol as a white solid. MS (ESI) m/z 318, 320 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59549-51-8, 5-Bromo-2-chloro-4-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia