Tag: M.W:100-200

Synthetic Route of 18592-13-7, 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.18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione, molecular formula is C5H5ClN2O2, molecular weight is 160.5584, as common compound, the synthetic route is as follows.

A mixture of 132 (0.170 g; 0.35 mmol), chloromethyluracil (0.061 g; 0.38 mmol), NaI (0.057 g; 0.38 mmol) and [K2CO3] (0.053 g; 0.38 mmol) in dimethylacetamide (8 [ML)] was heated at [80C] under argon atmosphere for 17 hours. The crude mixture was evaporated and purified by flash chromatography eluting with a gradient 2-8% of 3.5 N NH3 in MeOH/methylene chloride to give after trituration in ether/heptane Example 47 as a pale brown solid. Yield: 41% MS-ESI: 615 [[M+H] +] [‘H] NMR [(CDC13)] : 1.20-1. 40 (br m, 4H); 1.56 (br m, [4H)] ; 1.63 (s, 6H); 2.36 (s, 6H); 2.50 (br m, 8H); 3.29 (s, 2H); 3.58 (s, 2H); 4.15 (br m, 1H); 4.75 (br m, 1H); 5.53 (s, 1H) ; 6.80 (s, 1H) ; 6.96 (s, 1H) ; 7.21 (s, 2H); 7.97 (br s, 1H) ; 8.25 (s, 1H); 8.53 (br s, 1H).

The chemical industry reduces the impact on the environment during synthesis 18592-13-7, I believe this compound will play a more active role in future production and life.

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

Adding a certain compound to certain chemical reactions, such as: 17321-97-0, 2-Amino-4-methylpyrimidine-5-carbonitrile, 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, 17321-97-0, blongs to pyrimidines compound. COA of Formula: C6H6N4

General procedure: To the solution of corresponding quinazolone intermediate 13a(13b, 13c or 13d) in DCM (4 mL/1 mmol substrate)was added TFA (1mL/1 mmol substrate) dropwise at 0 C, and the resultant mixturewas stirred at room temperature. After 13a (13b, 13c or 13d) wastotally consumed, saturated NaHCO3 solution was added dropwiseat 0 C to adjust the PH value to 7. Following extraction with DCM,the organic layer was washed with brine, dried over anhydrousNa2SO4, and concentrated in vacuo to afford the Boc-deprotectedsecondary amine as slightly yellow solid.The mixture of corresponding Boc-deprotected secondaryamine (1.0 eq), 6-chloro-9H-purine (1.5 eq), DIPEA (4.0 eq) and t-BuOH (15 mL/1 mmol secondary amine) was stirred at 80 C underN2 atmosphere. After the secondary aminewas totally consumed, t-BuOH was removed in vacuo, and the residue was dissolved inDCM. The solution was washed with saturated NaHCO3 solution,dried over anhydrous Na2SO4, and concentrated in vacuo. Finally,the crude product underwent flash column chromatography (DCM/EA 5:1-1:1, V/V) to afford the purine derivative (14 or 15e17) aspale solid. Compounds with 4-aminopyrimidine-5-carbonitrile, 2-amino-6-methylpyrimidine-5-carbonitrile, 2-fluoro-9H-purine or2-chloro-9H-purine as HBs were prepared via similar procedure tothat for 14e17. However, the eluents utilized in the final flash columnchromatography of 21, 22, 24, 25 and 27 were different (DCM/EA 15:1-5:1, V/V, for 21, 24 and 27; DCM/EA 20:1-8:1, V/V, for22 and 25). The NMR spectra of 14e17, 28 and 29 indicated theexistence of rotamers.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17321-97-0, its application will become more common.

Reference:
Article; Chen, Yuqing; Fang, Fang; Gui, Shuangying; Hu, Yongzhou; Li, Jiaming; Liang, Jingtai; Liang, Xiao; Ma, Xiaodong; Meng, Chang; Tao, Qiangqiang; Wang, Huchuan; European Journal of Medicinal Chemistry; vol. 191; (2020);,
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

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

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

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

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

Application of 10070-92-5, 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde, molecular formula is C5H4N2O, 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.

Pyrimidine-5-formaldehyde (1.00 g, 9.25 mmol),2,4-Dimethylphenylhydrazine hydrochloride (1.60 g, 9.30 mmol)And DMF (16 mL) was added to a 100 mL single-neck round bottom flask in turn.Reaction at room temperature for 1 h,Neutralize the hydrochloride with 8 mL of saturated sodium bicarbonate solution, then add water (80 mL).A yellow solid precipitated, and the solid was filtered, washed with water (50 mL¡Á2).Dissolve in dichloromethane (20 mL), separate the layers, and collect the organic phase.The title compound was obtained as a yellow solid (1.20 g, 57.0%).

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:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Chen Kangzhi; Jin Chuanfei; Luo Ming; Zhang Yingjun; (28 pag.)CN108863948; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 24415-66-5 , The common heterocyclic compound, 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, 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.

Adding 85 mg (about 0.5 mmol) to a 10 mL microwave reaction tube.7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and 240 mg (about 1.5 mmol) of 1-ethyl-2-methyl-1H-indole,14 mg (about 10 mol%) of the catalyst bistrifluoromethylsulfonimide and 1 mL of the solvent HFIP, and then the microwave reaction tube was sealed.Then, the reactant in the microwave reaction tube was stirred at 100 C for 6 hours, and the solvent was distilled off under reduced pressure.And purified by column chromatography using DCM / MeOH as eluent to give about 107 mg of pure product e6, which was a purple solid with a yield of 73%;

The synthetic route of 24415-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Wang Shuai; Li Zhonghua; (21 pag.)CN109180684; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4595-59-9, 5-Bromopyrimidine, 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, 4595-59-9, blongs to pyrimidines compound. HPLC of Formula: C4H3BrN2

General procedure: A mixture of aryl bromides (0.5 mmol), potassium aryltrifluoroborates (0.6 mmol), K2CO3 (0.5 mmol), Pd(OAc)2 (1 mol %), EtOH/H2O (2 mL/2 mL) was stirred at 25 C in air for the indicated time. The reaction mixture was added to brine (15 mL) and extracted with ethyl acetate (3¡Á15 mL). The solvent was concentrated under vacuum, and the product was isolated by short-column chromatography on silica gel (200-300 mesh).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Article; Liu, Chun; Li, Xinmin; Gao, Zhanming; Wang, Xinnan; Jin, Zilin; Tetrahedron; vol. 71; 23; (2015); p. 3954 – 3959;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia