Day: September 10, 2021

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.113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, molecular formula is C7H10N2O4S, molecular weight is 218.23, as common compound, the synthetic route is as follows.HPLC of Formula: C7H10N2O4S

EXAMPLE 3 Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 2.86 g (10 mmol) of methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate were dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride was added. The mixture was stirred for 1 h. and then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added. After stirring at room temperature for 24 h., cautious hydrolysis was carried out with 10 ml of water, the pH was adjusted to 5 with acetic acid, and the solvent was removed by distillation under high vacuum. The residue was taken up in 100 ml of ethyl acetate, washed with water and dried over magnesium sulfate, and the solvent was distilled out. The residue was mixed with 10 ml of ether, and the resulting precipitate was filtered off with suction. After drying, 3.48 g (82%) of a white powder remained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BASF Aktiengesellschaft; US6030975; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1683-75-6, 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. 1683-75-6, name is 2-Amino-4-chloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below.

General procedure: To a mixture of (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1H-benzo[d]imidazole derivatives (7 mmol, 1 eq.), which was commercially available or prepared according to the literature procedure [WO2016192630], amino aromatic chloride (1.1 eq.) in DMF (20 mL) was added Na2CO3 aq. (3 eq.). The mixture was bubbled with Ar for 15 mins and then Pd(dppf)Cl2 (0.1 eq.) was added. The mixture was heated to 80oC and stirred for 4-6 hours under Ar atmosphere, then cooled to room temperature and concentrated to remove the organic solvent after reaction completion. The residue was diluted with water (100 mL) and extracted with EA (150 mL×3). The organic layer was separated and washed with saturated brine, then dried with anhydrous Na2SO4. The organic phase was then concentrated and the residue was further purified with flash chromatography or preparative HPLC to afford the desired intermediate compounds 3a-3j, which were characterized by LC-MS.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1683-75-6, 2-Amino-4-chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Zha, Chuantao; Deng, Wenjia; Fu, Yan; Tang, Shuai; Lan, Xiaojing; Ye, Yan; Su, Yi; Jiang, Lei; Chen, Yi; Huang, Ying; Ding, Jian; Geng, Meiyu; Huang, Min; Wan, Huixin; European Journal of Medicinal Chemistry; vol. 148; (2018); p. 140 – 153;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 335654-06-3, 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.335654-06-3, name is 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

N-lodosuccinimide (742 g, 3.30 mol) was added to 2-chloro-7H-pyrrolo[2,3-c/]pyrimidine (482.5 g, 3.14 mol) in acetonitrile (2500 mL) at 12C. The mixture was stirred at room temperature for 1 hour then sodium metabisulphite (650 g in 4500 mL of water) was added. The mixture was stirred for 1 hour then filtered to afford the title compound as a orange solid in 82% yield, 716.2 g. 1H NMR (400 MHz, DMSO-d6): delta ppm 7.83 (s, 1 H), 8.63 (s, 1 H), 12.73 (s, 1 H)

The chemical industry reduces the impact on the environment during synthesis 335654-06-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER LIMITED; ANDREWS, Mark, David; BAGAL, Sharanjeet, Kaur; BROWN, David, Graham; GIBSON, Karl, Richard; OMOTO, Kiyoyuki; RYCKMANS, Thomas; SABNIS, Yogesh; SKERRATT, Sarah, Elizabeth; STUPPLE, Paul, Anthony; WO2014/53967; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 287714-35-6, Adding some certain compound to certain chemical reactions, such as: 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate,molecular formula is C6H5ClN2O2, 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 287714-35-6.

1.3.1 Intermediate 10 ADiisopropylethylamine (1.5 mL, 8.7 mmol) was added to a mixture of methyl 2- chloropyrimidine-5-carboxylate (0.5 g, 2.9 mmol) and (3R)-3-methoxypyrrolidine hydrochloride (0.48 g, 3.48 mmol) in acetonitrile (6 mL) and the mixture was micro waved at 140 C for 30 min. The reaction was diluted with ethyl acetate (20 mL), water (10 mL) and sodium carbonate (sat., aq., 10 mL). The phases were separated and the aqueous phase was re- extracted with ethyl acetate (2 x 20 mL) and the combined organic phases were washed with water (10 mL), brine (2 x 10 mL), dried (MgS04), filtered and concentrated. The residue was purified by silica chromatography, 0-100% ethyl acetate in petrol to give product as a light yellow solid methyl 2-[(3R)-3-methoxypyrrolidin-l-yl]pyrimidine-5-carboxylate (0.66 g, 95 % yield). NMR (400 MHz, CD3OD) delta 8.80 (s, 2H), 4.10 – 4.16 (m, 1H), 3.86 (s, 3H), 3.71 – 3.81 (m, 2H), 3.55 – 3.70 (m, 2H), 3.36 (s, 3H), 2.04 – 2.24 (m, 2H)MS (ES+) 238

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. 287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; POONI, Parminder, Kaur; MERCHANT, Kevin, John; BUFFHAM, William, John; WO2011/83314; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 74502-83-3, 2-(Chloromethyl)-4,6-dimethylpyrimidine, 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, COA of Formula: C7H9ClN2, blongs to pyrimidines compound. COA of Formula: C7H9ClN2

A room temperature solution of 6-( i-methyl-i H-pyrazol-4-yl)-4-(6-(piperazin- 1- yl)pyridin-3 -yl)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile dihydrochloride (Example 2; 0.018 g, 0.0394 mmol) in dry DMF (0.3 mL) and TEA (54.9 tL, 0.394 mmol) was treated with 2-(2- bromoethoxy)propane (0.0197 g, 0.118 mmol). The reaction mixture was stirred overnight at 75C, and then additional 2-(2-bromoethoxy)propane (1 eq) and TEA (1 eq) were added. The reaction mixture was allowed to stir 24 h at 75 C. After cooling to room temperature, the resulting reaction mixture was directly purified by C18 reverse phase chromatography (5-99 o ACNwater as the gradient eluent) to afford the title compound (7.4 mg, 41o yield). MS (apci) mz = 471.2 (M+H).used only 1.5 eq of the alkyl halide (2-(chloromethyl)-4,6-dimethylpyrimidine),10 eq of TEA, and was conducted at room temperature, but otherwise followed a similar procedure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,74502-83-3, 2-(Chloromethyl)-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); 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.157335-97-2, name is 5-Bromo-4,6-dimethylpyrimidine, molecular formula is C6H7BrN2, molecular weight is 187.0372, as common compound, the synthetic route is as follows.Product Details of 157335-97-2

Under Ar(g), to a mixture of pyrazin-2-amine (1) (209mg, 2.2mmol), 5- bromo-4,6-dimethylpyrimidine (2) (374mg, 2.0mmol), Cs2C03 (1.30g, 4.0mmol) was added degassed dry 1 ,4-dioxane (13mL). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt. EtOAc (15ml_), H20 (10mL) and brine (5mL) were added to the reaction mixture. The organic phase was separated and the aqueous phase was extracted with EtOAc (15ml_). The organic layers were combined and Pd-scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (43mg, 1 1 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,157335-97-2, 5-Bromo-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 63558-65-6 ,Some common heterocyclic compound, 63558-65-6, molecular formula is C4H2ClIN2, 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-amino-2,5-difluorophenol (0.190 g, 1.310 mmol) in DMF ( 10 mL) was added potassium ter/-butoxide (0.168 g, 1.497 mmol). The mixture was stirred at RT for 30 min. 4-Chloro-5-iodopyrimidine (0.30 g, 1.248 mmol) was added and the reaction mixture was heated at 80 C overnight. The reaction mixture was quenched with water and the solution was extracted with EtOAc (3x). The organic solution was washed with 5% aqueous lithium chloride solution and brine. The organics were dried over gS04, filtered, and concentrated. The crude was purified by silica gel column chromatography ( 10% to 50%EtOAc/hexane) to obtain 2,5-difluoro-4-(5-iodopyrimidin-4-yloxy)benzenamine (160 mg, 36.7%) yield) which was used for the next reaction. MS (ESI) m/z: 349.9 (M+H+).

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. 63558-65-6, 4-Chloro-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; FLYNN, Daniel, L.; KAUFMAN, Michael, D.; WO2011/139891; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, 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 C5H4Cl2N4O, blongs to pyrimidines compound. Computed Properties of C5H4Cl2N4O

Intermediate 1 RRN 104-[2-Amino-6-chloro-5-(formylamino)pyrimidin-4-yl]piperazine-1-carboxylic acid tert-butyl ester [0221] To a suspension of N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (10.0 g, 48.3 mmol) in 1,4-dioxane (400 mL) were added N,N-diisopropylethylamine (12.7 mL, 72.5 mmol) and piperazine-1-carboxylic acid tert-butyl ester (9.8 g, 53.1 mmol). The mixture was stirred at 55 C. for 1 h. The solvent was removed in vacuo and the residue was partitioned between DCM and water. The aqueous phase was extracted with further DCM and the combined organic fractions were washed with brine, then dried (Na2SO4) and evaporated in vacuo to give the title compound (17.1 g, 100%) as a white solid. LCMS (ES+) 357.4 (M+H)+, RT 1.08 minutes (method 3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, and friends who are interested can also refer to it.

Reference:
Patent; Brookings, Daniel Christopher; Ford, Daniel James; Franklin, Richard Jeremy; Ghawalkar, Anant Ramrao; Kulisa, Claire Louise; Neuss, Judi Charlotte; Reuberson, James Thomas; US2014/315885; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1193-21-1, 4,6-Dichloropyrimidine, 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: 1193-21-1, blongs to pyrimidines compound. Recommanded Product: 1193-21-1

298 mL of methanol is added to 387 mL (7.98 mol) of hydrazine monohydrate, and the mixture is cooled to 10C (internal temperature). To this mixed solution is gradually added 149 g (1.00 mol) of 4,6-dichloropyrimidine (at an internal temperature of 20C or lower), then the ice bath is removed to increase the temperature to room temperature, followed by stirring at the same temperature for 30 minutes. Thereafter, the mixture is further heated to an internal temperature of 60C, and is stirred at the same temperature for 5 hours. After completion of the reaction, 750 ml of water is added thereto, and then the mixture is cooled to an internal temperature of 8C with ice. Crystals precipitated are collected by filtration, spray-washed with water, then spray-washed with isopropanol. The crystals are dried at room temperature for 36 hours to obtain 119 g (white powder; yield: 84.5%) of the intermediate (28). Results of NMR measurement of the thus-obtained intermediate (28) are as follows. 1H-NMR (300 MHz, d-DMSO) 7.80 (s, 1H), 7.52 (s, 2H), 5.98 (s, 1H), 4.13 (s, 4H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1193-21-1, 4,6-Dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; FUJIFILM Corporation; EP2253672; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 945950-37-8, 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 945950-37-8, name is 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Suspended in 30mL of DCM was 4-methyl -7H- pyrrolo [2,3-d] pyrimidine (1g, 7.51mmol) was added N- iodosuccinimide (1.86g, 8.26mmol).It was stirred at room temperature for 2 hours the reaction mixture.The volatiles were removed in vacuo.Of anhydrous ethyl acetate and 50% saturated NaHCO3The residue obtained was extracted.With water and the organic layer was washed with brine, dried (MgSO4), Filtered and the volatiles removed in vacuo.The residue was suspended in acetonitrile and sonicated for 45 minutes.The solid was collected by filtration to give 5-iodo-4-methyl–7H- pyrrolo [2,3-d] pyrimidine (1.69 g).

According to the analysis of related databases, 945950-37-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pulaixike Company; Zhang, Chao; Ibrahim, Prabha N; Nespi, Marika; Shi, Songyuan; Spevak, Wayne; Habets, Gaston G; Burton, Elizabeth A; Hirth, Klaus-Peter; (181 pag.)CN105228983; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia