Pyrimidines

Synthetic Route of 69034-12-4, 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.69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

General procedure: To a solution of 12 (1000 mg, 4.71 mmol) in NMP (9.4 ml) was acdded ethyl 2-chloropyrimidine-5-carboxylate (967 mg,5.18 mmol) and diisopropyl ethylamine (913 mg, 7.07 mmol) at room temperature. The reaction mixture was stirred at 80 C for 5 h. The reaction mixture was diluted with water to afford the white precipitation. The resulting solid was collected by filtration to afford 13c (1627 mg, 95.3%) as the white solid.

Statistics shows that 69034-12-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-(trifluoromethyl)pyrimidine.

Reference:
Article; Tsuno, Naoki; Yukimasa, Akira; Yoshida, Osamu; Suzuki, Shinji; Nakai, Hiromi; Ogawa, Tomoyuki; Fujiu, Motohiro; Takaya, Kenji; Nozu, Azusa; Yamaguchi, Hiroki; Matsuda, Hidetoshi; Funaki, Satoko; Yamanada, Natsue; Tanimura, Miki; Nagamatsu, Daiki; Asaki, Toshiyuki; Horita, Narumi; Yamamoto, Miyuki; Hinata, Mikie; Soga, Masahiko; Imai, Masayuki; Morioka, Yasuhide; Kanemasa, Toshiyuki; Sakaguchi, Gaku; Iso, Yasuyoshi; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2177 – 2190;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 90349-23-8, 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. 90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

A solution of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (120 mg, 0.62 mmol), HOBt (125 mg, 0.93 mmol), EDCI (144 mg, 0.93 mmol) in DMF (5 mL) was stirred at room temperature for 30 min and charged with 4-ethynylcyclohexan-l -amine (92 mg, 0.75 mmol) and stirred for another 16 h at room temperature. The reaction mixture was diluted with water (10 mL), extracted with ethyl acetate (3 X 10 mL), dried over a2S04and concentrated in vacuo. The crude compound which was purified by FCC (eluent, 2-4% methanol in DCM) to afford the title compound as a white solid (120 mg, 65%).XH NMR (400 MHz, CDC13) delta 8.61 (s, 1H), 8.04 (d, J=5.73 Hz, 1H), 6.70 (br s, 1H), 4.06-4.16 (m, 1H), 2.78(s, 3H), 2.67 (s, 1H), 2.63 (s, 3H), 2.29-2.41 (m, 1H), 2.16 (d, J=10.58 Hz, 2H), 2.12-1.84 (m, 2H), 1.34-1.43 (m, 2H), 1.22-1.31 (m, 2H). ES-MS m/z 297.25 (M+H)+. HPLC purity 99.9%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-66-9, 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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide, molecular formula is C5H4ClN3O, 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.

3.3. 2-{[3-{3-[(4-Fluorophenoxy)methyl]-1-piperidyl}propyl]}amino}pyrimidine-4-carboxamide 5.09 g (0.015 mol) of 3-[(4-fluorophenoxy)methyl]-1-piperidinepropanimine hydrochloride, 2.36 g of 2-chloropyrimidine-4-carboxamide, 7.26 g (0.0525 mol) of K2 CO3 and 0.2 g of sodium iodide are suspended in 450 ml of DMF. The reaction mixture is stirred under argon for 21 h, poured into 200 ml of water and extracted 3 times with ethyl acetate. The organic phase is washed with water, dried, filtered and evaporated. 3.35 g of product are obtained, which product is reacted with 1 g of fumaric acid in an ethanol/ethyl ether mixture.

According to the analysis of related databases, 22536-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Synthelabo; US5210086; (1993); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 33034-67-2, Adding some certain compound to certain chemical reactions, such as: 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine,molecular formula is C5H2ClF3N2, 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 33034-67-2.

Step 1: To a solution of (R)-3-isopropylpiperazin-2-one hydrochloride (2.61 g, 14.62 mmol) and iPr2NEt (7.60 mL, 43.86 mmol) in DMF (20 mL) was added a solution of 2-chloro-4- (trifluoromethyl)pyrimidine (3.47 g, 19.00 mmol) in DMF (2 mL). The resulting solution was stirred at 100 ¡ãC under N2 for 3 h at which point the reaction was deemed complete by LC- MS. Sat. aq. NH4C1 (30 mL) was added to quench the reaction, followed by addition of EtOAc (30 mL). The EtOAc layer was separated and the aqueous layer was extracted with EtOAc (3 x 20 mL). The EtOAc layers were combined, dried using Na2S04 and evaporated to give nearly pure crude product. Purification on a silica cartridge using ISCO FCC eluting with 100percent EtOAc gave 4.03 grams of (R)-3-isopropyl-4-(4-(trifluoromethyl)pyrimidin-2- yl)piperazin-2-one (96percent) as a slightly orange thick oil.LC-MS m/z 289.17 [M + H]+ 1H NMR (CDCI3, 400MHz): delta 8.52 (d, / = 4.8 Hz, 1H), 6.82 (d, / = 4.4 Hz, 1H), 6.56 (br, 1H), 5.20 (d, / = 6.8 Hz, 1H), 4.83-4.77 (m, 1H), 3.55-3.37 (m, 3H), 2.49-2.41 (m, 1H), 1.15 (d, J = 6.8 Hz, 3H), 1.04 (d, / = 6.8 Hz, 3H).

According to the analysis of related databases, 33034-67-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; DONG, Chengguo; FAN, Yi; LEFTHERIS, Katerina; LOTESTA, Stephen; SINGH, Suresh, B.; TICE, Colin; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2013/138565; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 137281-39-1, 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. 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, molecular formula is C15H14N4O3, 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.

10.00 g of acid (2) from the example 4 are added at room temperature to 90ml of ethanol, 40 ml of water and 8.83 g of 2-chloro-4,6-dimethoxy-1 ,3,5-triazine(CDMT).A mixture consisting of 21.1 g NaOH, 20 ml of water and 10.3 ml of N-10 methyl morpholine was first added to the suspension obtained and then 10,45 g ofdiethyi-L-glutamate hydrochloride.The reaction mixture is kept under stirring at 40C for 3 hours and is filteredon a bed consisting of 0,48 g of activated carbon and 0:48 g of Celite. Afterwashing the filter with 20 ml of ethanol/water mixture 3/2, the filtrate is heated to15 40C and added to 49 ml of water and 55 ml of Acetone.The mixture is then cooled to room temperature and after cooling to ooc for1 hour, the suspension obtained is filtered, the solid washed with 80 ml ofwater/acetone mixture 3/1 and with 80 ml of Acetone. The solid is then dried undervacuum at 50C. 14:25 g of diethyl ester of pemetrexed (3) as a cream-colored20 solid (yield 93.5%) are obtained.

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 137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid.

Reference:
Patent; BERLIN-CHEMIE AG; BONACCORSI, Fabrizio; CALVANI, Federico; PASQUI, Franco; WO2014/24164; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 100644-65-3 ,Some common heterocyclic compound, 100644-65-3, molecular formula is C5H4ClN5, 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 192. 4-Chloro-1-(4-chloro-3,5-diemthyl-pyridin-2-ylmethyl)-1H- pyrazolo [3, 4-D] PYRIMIDIN-6-YLAMINE A mixture OF 4-CHLORO-LH-PYRAZOLO [3, 4-D] PYRIMIDIN-6-YLAMINE (158 mg), crude 4-chloro-2-chloromethyl-3,5-dimethyl-pyridine (204 mg), CS2C03 (660 mg) and DMF was heated to 80 C for 1.5 h, diluted with EtOAc and washed with water. The crude material was concentrated and suspended in MEOH/DCM. Filtration gave a 2: 1 mixture of regioisomers which was further purified by preparative silica gel plate (EtOAc 100%). The major (less polar) isomer corresponded to the title compound. R. t. 5.45 MIN. H- NMR (CDC13) 8 8.22 (s, 1H), 7.90 (s, 1H), 5.57 (s, 2H), 5.28 (s, 2H), 2.43 (s, 3H), 2.31 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100644-65-3, its application will become more common.

Reference:
Patent; CONFORMA THERAPEUTICS CORPORATION; WO2005/28434; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1780-40-1 , The common heterocyclic compound, 1780-40-1, name is 2,4,5,6-Tetrachloropyrimidine, molecular formula is C4Cl4N2, 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 2,4,5,6-tetrachloropyrimidine (5 g, 22.9 mmol) in THF (50 mL) was added 1N NaOH (31 mL, 31.2 mmol) dropwise, and the mixture was stirred overnight at RT. The solution was acidified with 1N HCl and extracted with DCM (3x). The organics were combined, dried, and concentrated in vacuo. The solids were slurried in Et2O for 30 min at RT, filtered, washed with Et2O, and dried to give 3.0 g (66%) of the title compound. [M+H] Calc?d for C4HCl3N2O, 201; Found, 201.

The synthetic route of 1780-40-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE CORPORATION; XU, Jiangchun; CHO, Robert; NGUYEN, Aaron; (297 pag.)WO2018/31658; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 34289-60-6, 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 34289-60-6 as follows.

In a 25 ml round bottom flask with stirring bar was combined 2-hydroxy-4,6- dimethylpyrimidine hydrochloride, 2.05 g, cesium carbonate, 5.5g, and dimethyl formamide, 8.5 ml. The mix was stirred 30 minutes, then intermediate 1 c, 1.3g, was added. The resulting mix was heated at 80 0C overnight. TLC with 1 : 1 ethyl acetate/hexanes on silica showed complete conversion to new lower RF spot. The reaction was diluted with water, and extracted with ethyl acetate. The organic layer was washed twice with water. The combined aqueous layers were back extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated in vacuo to provide methyl 9-{3-[(4,6-dimethylpyrimidin-2-yl)oxy]propyl}- 2,3,4,9-tetrahydro-lH-carbazole-6-carboxylate as an orange oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34289-60-6, its application will become more common.

Reference:
Patent; ITHERX PHARMACEUTICALS, INC.; WO2009/103022; (2009); 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. 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H8ClN3O2, 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. Computed Properties of C9H8ClN3O2

Step 4. To crude mixture 4-4 in ethanol (1.07mL), A-1-6A (48.47 mg, 0.2148 mmol) was added. The mixture was stirred at 80 C for 2 hours. Water (5mL) was added and extracted with DCM (3 x 5mL). The combined organic phase was washed with brine and then dried over Na2S04. Flash column chromatography (ISCO system, 12g, 0-40% ethyl acetate in hexanes) provided 4-5A (19 mgs, 14.84 % yield), and 4-5B (10.5 mg, 8.2 % yield).

With the rapid development of chemical substances, we look forward to future research findings about 1224944-77-7.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; UNG, Jane; (108 pag.)WO2018/22911; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 36315-01-2, 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 36315-01-2, name is 2-Amino-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.

According to the analysis of related databases, 36315-01-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Ren-Jun; Ren, Tongtong; Gao, Jie-Yu; Wang, Li; Yu, Qilin; Yao, Zheng; Song, Guo-Qing; Ruan, Wei-Bin; Niu, Cong-Wei; Song, Fu-Hang; Zhang, Li-Xin; Li, Mingchun; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 348 – 363;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia