Pyrimidines

Electric Literature of 18592-13-7, 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. 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

A mixture of 18 (0.252 g; 0.5 mmol), 6-chloromethyluracil (0.088g ; 0.55 mmol), K2CO3 (0.076 g; 0.55 mmol) and NaI (0.082 g; 0.55 mmol) in acetonitrile (5 ml) was heated at [85C] under argon atmosphere for 4 hours. The mixture was purified by flash chromatography eluting with a gradient of 5-10 % [MEOH/CH2C12] to give Example 11 as a solid. Yield: 63 [%] [‘H] NMR [(CDC13)] : 1.2-1. 4 (m, 4H); 1.6 (s, 6H); 1.4-1. 8 (m, 4H); 2.34 (s, 6H); 2.4-2. 7 (m, 10H); 2.85-2. 95 (m, 2H); 3.3 (s, 2H); 4-4.2 (m, br, 1H); 4.6-4. 8 (m, br, 1H); 5.53 (s, 1H); 6.72 (s, 1H) ; 6.93 (s, 1H); 7.04 (s, 2H); 8.05-8. 2 (m, 2H). MS-ESI: 629 [M+H] [+]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18592-13-7, 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/18480; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 24415-66-5, 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. 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, 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.

The preparation method of the compound e10 comprises the steps of: taking about 1 mmol of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and about 3 mmol.1-benzyl-1H-indole was added to a 10 mL microwave reaction tube,Further, 2 mL of hexafluoroisopropanol solvent and about 0.1 mmol of bistrifluoromethanesulfonimide catalyst were added, sealed and heated to 100 C with stirring and reacted for about 6 h.Then, the reaction system was monitored by TLC, and after the reaction system was cooled to room temperature, it was separated and purified by column chromatography to obtain pure compound e10.The compound e10 is a yellow solid with a yield of 90%.

According to the analysis of related databases, 24415-66-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Zheng Yichao; Yuan Shuo; Shen Dandan; (27 pag.)CN109020976; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1500-85-2, 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.1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, molecular weight is 134.14, as common compound, the synthetic route is as follows.

To a solution of 200 mg (1.49 mmol) of 7H-pyrrolo[2,3-d]pyrimidin-4-amine in 4 mL of DMF, 235 muL of dimethylformamide dimethyl acetal were added. The mixture was stirred at room temperature overnight. The solvent was then removed in vacuo and the residue taken up with DCM, washed with brine, dried over anhydrous Na2SO4and evaporated to dryness. The crude was triturated with diisopropylether and filtered, to afford 204 mg (73%) of the title compound. 1H NMR (600 MHz, DMSO-cie) delta ppm 3.10 (s, 3 H) 3.16 (s, 3 H) 6.45 (dd, J=3.39, 1.92 Hz, 1 H) 7.21 (dd, J=3.11 , 2.38 Hz, 1 H) 8.28 (s, 1 H) 8.79 (s, 1 H) 11.60 (br. s., 1 H) HRMS (ESI) calcd for C9HnN5 [M+H]+ 190.1087, found 190.1085.

The chemical industry reduces the impact on the environment during synthesis 1500-85-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; ANGIOLINI, Mauro; BUFFA, Laura; MENICHINCHERI, Maria; MOTTO, Ilaria; POLUCCI, Paolo; TRAQUANDI, Gabriella; ZUCCOTTO, Fabio; WO2014/184069; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 33034-67-2, 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.33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

Step 4: The product of Step 3 (460 mg, 1.720 mmol), 2-chloro-4-(trifluoromethyl)pyrimidine (314 mg, 1.638 mmol), Xantphos (284 mg, 0.492 mmol), palladium (II) acetate (73.6 mg, 0.328 mmol), cesium carbonate (1.068 g, 3.28 mmol) and dioxane (12.3 mL) were heated at 90 ¡ãC for 90 minutes. The reaction mixture was diluted with ethyl acetate, washed with water and dried over Na2S04. Filtration and solvent evaporation gave a residue which was further purified by column chromatography on silica gel, eluting with 40percent ethyl acetate in hexane to afford l-[5-(3- cMoro-5-{[4-(trifluoromemyl)pyrimidin-2-yl^ as a brown solid (390 mg, 55.8percent). NM (500 MHz, CDCI3): 5 8.71 (d, J – 4.7 Hz, 1 H); 7.92(s, 1 H); 7.85 (s, 1 H); 7.78 (s, 1 H); 7.69 (s, 1 H); 7.25 (s, 1 H); 7.13 (d, J= 4.8 Hz, 1 H); 3.81 (s, 1 H); 2.73 (s, 2 H); 2.58-2.47 (m, 2 H); 2.13-1.97 (m, 2 H) MS APCI: [M+H]+ m/z 427.1. rhSYK activity = ++

The chemical industry reduces the impact on the environment during synthesis 33034-67-2, I believe this compound will play a more active role in future production and life.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4983-28-2, 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. 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine. A new synthetic method of this compound is introduced below.

A stirred mixture of 2-chloro-5-pyrimidinol (107) (1.00 g, 7.66 mmol) and chloromethyl ethyl ether (1.75 mL, 18.9 mmol) in anhydrous DMF (2.5 mL) was treated with K2CO3 (2.15 g, 15.6 mmol). After stirring at room temperature for 16 h, the mixture was added to ice/aqueous NaHCO3 (100 mL) and extracted with 50% Et2O/petroleum ether (5¡Á100 mL). The combined extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-1% Et2O/petroleum ether firstly gave foreruns, and then further elution with 1-10% Et2O/petroleum ether gave 2-chloro-5-(ethoxymethoxy)pyrimidine (108) (1.27 g, 88%) as an oil; 1H NMR (CDCl3) delta 8.43 (s, 2H), 5.27 (s, 2H), 3.74 (q, J=7.1 Hz, 2H), 1.23 (t, J=7.1 Hz, 3 H); HRESIMS calcd for C7H10ClN2O2 m/z [M+H]+ 191.0396, 189.0425, found 191.0397, 189.0426.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4983-28-2, its application will become more common.

Reference:
Patent; Global Alliance for TB Drug Development; US2011/28466; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 73418-88-9, 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. 73418-88-9, name is Methyl 5-aminopyrimidine-2-carboxylate. A new synthetic method of this compound is introduced below.

Methyl 5-aminopyrimidine-2-carboxylate (10.29 mg, 0.067 mmol) and pyridine (0.049 mL, 0.611 mmol) were dissolved in DCM (2 mL) Intermediate 816C (0.030 g, 0.06 1 mmol) was added as a solution in DCM (1 mL). The reaction mixture was allowedto stir for 1 hour. The reaction mixture was concentrated under reduced pressure and purified on ISCO using 24 g column eluting with 0-100% EtOAc over 15 mm to yield Intermediate 816D (24.6 mg, 0.040 mmol, 66.3 % yield) as a pale yellow solid. ?HNIVIR (400MHz, CDC13) 8.47 (d, J=1.8 Hz, 3H), 8.44 (s, 1H), 7.91 (d, J10.3 Hz, 1H), 7.66 (s, 1H), 7.13 (s, 1H), 5.70-5.60 (m, 1H), 5.31 (br. s., 1H), 2.56 (s, 3H), 1.41 (d, J=6.8 Hz,5H), 1.17 (s, 3H), 0.07-0.11 (m, 6H). LC-MS. method H, RT = 1.27 mm, MS (ESI)m/z:608.0 (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,73418-88-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-65-8, 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 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(A)A mixture of 2-chloro-5-methoxypyrimidine (10 g, 69.44 mmol, 1 eq) MeOH-CH3CN 4:1 (160 ml -40ml), TEA (20 ml) and Pd(dppf)Cl2 DCM (6 g, 7.34 mmol, 0.1 eq) in an autoclave, was stirred at 100C for18 h under CO gas atmosphere. The RM was cooled to RT, filtered through celite, washed with MeOH(100 ml), and the filtrate was concentrated. The residue upon purification by CC (silica gel; EtOAc – PE;3:7) afforded methyl 5-methoxypyrim idine-2-carboxylate (6 g, 52%).

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 22536-65-8, 2-Chloro-5-methoxypyrimidine.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1059735-34-0, 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 1059735-34-0, name is 7-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 7-benzyl-2,4-dichloro-6,8-dihydro-5H- pyrido[3,4- (JJpyrimidine (17.3 g, 58.8 mmol) in DMSO (200 mL) was added DIEA (19.0 g, 147 mmol) and tert-butyl piperazine- 1 -carboxylate (11.5 g, 61.7 mmol) and the mixture stirred at 55 C for 10 hours. The reaction mixture was poured into ethyl acetate (200 mL) and washed with water (3x200mL). The combined organics were washed with brine (200 mL), dried over anhydrous Na2S04 and concentrated under vacuum to give a residue. The residue was purified by trituration from MTBE (200 mL) to give tert-butyl 4-(7-benzyl-2-chloro-6,8-dihydro-5H- pyrido[3,4-d]pyrimidin-4-yl) piperazine- 1 -carboxylate (24 g, 52.9 mmol). ES+APCI MS m/z 444.2 [M+H]+.

According to the analysis of related databases, 1059735-34-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; FISCHER, John, P.; FELL, Jay, Bradford; BLAKE, James, F.; HINKLIN, Ronald, Jay; MEJIA, Macedonio, J.; HICKEN, Erik, James; CHICARELLI, Mark, Joseph; GAUDINO, John, J.; VIGERS, Guy, P.A.; BURGESS, Laurence, E.; MARX, Matthew, Arnold; CHRISTENSEN, James, Gail; LEE, Matthew, Randolf; SAVECHENKOV, Pavel; ZECCA, Henry, J.; (529 pag.)WO2017/201161; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 28732-79-8, 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 28732-79-8, name is 4-Chloropyrido[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 20 (400 mg, 0.89 mmol) was dissolved in DCM (23 mL) and TFA (4.1 mL) was added. The mixture was stirred at r.t. for 1.5 h and excess DCM and TFA were removed in vacuo. The yellow residue obtained was basified using 0.2M aqueous NaOH (40 mL) and extracted with EtOAc (3 x 80 mL). The combined organic layers were dried (MgS04) and concentrated in vacuo. Purification by column chromatography on silica, eluting with DCM/MeOH/NH3 (95:4:1), gave a colourless gum (278 mg, 90%). deltaEta (CDC13) 7.94 (IH, s), 7.52 (IH, dd, J 8.8, 6.1 Hz), 7.15 (IH, t, J 8.9 Hz), 5.11 (IH, br s), 4.98 (IH, br s), 3.80-3.76 (2H, m), 3.75 (3H, s), 3.70-3.59 (2H, m), 3.56-3.42 (2H, m), 3.21-3.07 (2H, m), 2.59 (3H, d, J 2.40 Hz), 1.54 (3H, s). LCMS (ES+) 347 (M+H)+. A solution of this gum (55.6 mg, 0.161 mmol), 4-chloropyrido[2,3-i?pyrimidine (40 mg, 0.24 mmol) and DIPEA (0.084 mL, 0.48 mmol) in ?-butanol (1 mL) was heated to 130C under microwave irradiation for 1 h. Purification by preparative HPLC afforded the title compound (41 mg, 54%) as a white solid. deltaEta (DMSO-Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2011/58108; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 10070-92-5, Adding some certain compound to certain chemical reactions, such as: 10070-92-5, name is Pyrimidine-5-carbaldehyde,molecular formula is C5H4N2O, 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 10070-92-5.

General procedure: A mixture of the appropriate amine (1M-3M, 2 mmol) and the appropriate aldehyde (2.2 mmol) in ethanol (10 mL) was stirred at room temperature for 8 h.

According to the analysis of related databases, 10070-92-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Da-Jun; Sun, Wen-Fang; Zhong, Zhao-Jin; Gao, Rong-Mei; Yi, Hong; Li, Yu-Huan; Peng, Zong-Gen; Li, Zhuo-Rong; Molecules; vol. 19; 1; (2014); p. 925 – 939;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia