Tag: M.W:100-200

Related Products of 35808-68-5, 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. 35808-68-5, name is 4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (500 mg, 3.27 mmol) in DMF (5 mL) caesium carbonate (2.13 g, 6.54 mmol) and benzensulfonyl chloride (417 mu, 3.27 mmol) were added. The mixture was stirred at room temperature for 1.5 hours, then diluted with ethylacetate and washed with water and brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The residue was chromatographed on a silica gel column eluted with dichloroethane/ethylacetate 7/3 affording 761 mg (79%) of 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (cmpd (XVIII), step h). To a solution of 2M in THF lithium diisopropylamide (0.83 mL, 1.65 mmol) in dry THF (5 mL) cooled to -78C, under argon atmosphere, the last intermediate (400 mg, 1.37 mmol) dissolved in 5 mL of dry THF, was added dropwise during 10 minutes. The mixture was maintained in these conditions for 1 hour and then methyl iodide was added (0.11 mL, 1.78 mmol). The mixture was stirred 2 hours and during this time further 0.21 mL of methyl iodide were added. After 4 hours the temperature was driven to -10C and a saturated aqueous solution of ammonium chloride was added. The product was then extracted with ethylacetate, the organic layer dried over Na2S04 and evaporated affording 4-chloro-6-methyl-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (cmpd (XX), step i). This intermediate (1.37 mmol) was dissolved in 10 mL of THF and 5 mL of methanol and 0.5 g of sodium hydrate were added. The mixture was stirred at room temperature for 1 hour, then the solvent removed in vacuo. The residue was taken up with ethylacetate and washed with a saturated aqueous solution of ammonium chloride and extracted again with ethylacetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated, .giving 223 mg of 4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine (cmpd (XXI), step j). This intermediate (1.37 mmol) was dissolved in chloroform (10 mL) and N-iodo succinimide (308 mg, 1.37 mmol) was added. The mixture was refluxed for 1.5 hours, cooled to room temperature, diluted with dichloromethane, washed with aqueous Na2S203 and ammonium chloride. The organic layer was dried over Na2S04 and evaporated. The residue was chromatographed on a silica gel column 1 ,2-dichloroethane/ethylacetate 6/4, giving 110 mg of 4-chloro- 5- iodo-6-methyl-7H-pyrrolo[2,3-d]pyrimidine (cmpd (XXII), step d). The last intermediate (0.39 mmol) was dissolved in DMF (3 mL) and additioned with caesium carbonate (257 mg, 0.79 mmol) and iodoethane (47 mu, 0.59 mmol). The mixture was stirred at room temperature for 2 hours, thenpoured into water and extracted twice with ethylacetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was finally puriufied by chromatography on a silica gel column eluted with dichloromethane/ethylacetate giving 51 mg of 4-chloro-7-ethyl-5-iodo-6-methyl-7H-pyrrolo[2,3-d]pyrimidine (cmpd (IV), step e). 1H NMR (401 MHz, DMSO-d6) delta ppm 1.24 – 1.32 (m, 3 H) 2.54 (s, 3 H) 4.36 (q, J=7.16 Hz, 2 H) 8.58 (s, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,35808-68-5, its application will become more common.

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

Synthetic Route of 54198-72-0 ,Some common heterocyclic compound, 54198-72-0, molecular formula is C7H10N2O, 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.

Synthesis of 2-(chloromethyl)-4, 6-dimethylpyrimidine: [0593] To a stirred solution of (4, 6-dimethylpyrimidin-2-yl) methanol (285 mg, 2.06 mmol) in chloroform (8 mL) under argon atmosphere was added phosphoryl chloride (792 mg, 5.16 mmol) at 0 C; heated to 65 C and stirred for 3 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was neutralized with saturated sodium bicarbonate solution (15 mL) and extracted with CH2CI2 (2 x 25 mL). The combined organic extracts were dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude 2-(chloromethyl)-4, 6- dimethylpyrimidine (225 mg, 68%) as semi solid. The crude was carried to the next step without any further purification. [0594] 1H-NMR (CDCI3, 400 MHz): delta 7.48 (s, 1H), 5.00 (s, 2H), 2.8 (s 6H); LC- MS: 88.37%; 157 (M++l); (column: X Bridge C-18, 50 3.0 mm, 3.5 mupiiota); RT 2.05 min. 0.05% TFA in water: ACN; 0.8 mL/min); TLC: 20% EtOAc/ Hexanes (R/. 0.7)

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. 54198-72-0, (4,6-Dimethylpyrimidin-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 7226-23-5 ,Some common heterocyclic compound, 7226-23-5, molecular formula is C6H12N2O, 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 1 3-Cyclopentyl-2-(4-ethynyl-phenyl)-N-thiazol-2-yl-propionamide A solution of diisopropylamine (11.2 mL, 80.13 mmol) in tetrahydrofiran (120 mL) cooled to -78 C. was treated with a 2.5M solution of n-butyllithium in hexanes (32 mL, 80.13 mmol). This solution was stirred at -78 C. for 30 min and then treated with a solution of (4-iodo-phenyl)-acetic acid (9.67 g, 36.9 mmol) in tetrahydrofuran (88 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (29 mL). The reaction mixture was allowed to stir at -78 C. for 1 h. At this time, the reaction was treated with iodomethylcyclopentane (8.53 g, 40.6 mmol). The reaction mixture was allowed to slowly warm to 25 C. where it was stirred at 25 C. for 18 h. At this time, the reaction mixture was quenched with water (5 mL) and then concentrated in vacuo. The residue was diluted with water (800 mL) and then acidified to pH=2 with concentrated hydrochloric acid. This solution was extracted with ethyl acetate (2*800 mL). The combined organic extracts were washed with water (1*600 mL) and a saturated aqueous sodium chloride solution (1*600 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid (7.34 g, 57.8%) as a white solid: mp 105-107 C.; EI-HRMS m/e calcd for C14H17IO2 (M+) 344.0273, found 344.0275.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7226-23-5, its application will become more common.

Reference:
Patent; Mahaney, Paige E.; US2001/53851; (2001); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. category: pyrimidines

Dissolve 4-chloro-pyrrolo[2,3-d]pyrimidine (20 mmol) in DMF (6 mL), add NBS or NCS (21 mmol) in portions on ice bath, react at room temperature for 12 h, and pour the reaction mixture into 80 mL of ice. In the water, a large number of off-white solids precipitated and were filtered. The filter cake was washed with 15 mL of water and dried to give Intermediate 2. 4-Chloro-5-bromo-pyrrolo[2,3-d]pyrimidine (2b) Off-white solid, yield 95%

With the rapid development of chemical substances, we look forward to future research findings about 3680-69-1.

Reference:
Patent; Shandong University; Zhao Guisen; Yang Dezhi; Liu Meixia; Zhang Zhen; Zhang Qian; Yang Qingtao; (36 pag.)CN107556318; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 29274-24-6

To 5-chloropyrazolo[l,5-a]pyrimidine (200 mg, 1.31mmol) in 1.5ml DMF was added POCI3 (358 3.92 mmol). The reaction was stirred at room temperature overnight. The mixture was cooled to 0 C in ice bath and the then neutralized with 6M NaOH. The solid formed was isolated by filtration and air dried to give 165 mg of 5-chloropyrazolo[l,5- a]pyrimidine-3-carbaldehyde as yellow solid (70% yield). LCMS (M+l=182)

The synthetic route of 29274-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYLENE PHARMACEUTICALS INC.; HADDACH, Mustapha; RYCKMAN, David; RAFFAELE, Nicholas; WO2011/31979; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 287714-35-6, 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. 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, 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.

4-(N-Boc-amino)piperidine 9.3 g was added to a 250 mL three-necked flask.N,N-dimethylacetamide 100mL,N,N-diisopropylethylamine 7.5 g,2-chloropyrimidine-5-carboxylic acid methyl ester 4.0 g,Stir at room temperature for 3 h under nitrogen.The end of the reaction was monitored by TLC (petroleum ether: ethyl acetate = 2:1).200 mL of water was added and extracted with dichloromethane (100 mL x 3), and the organic phases were combined.The organic phase was washed successively with 5% dilute hydrochloric acid (100 mL¡Á3) and saturated sodium chloride (100 mL¡Á3).The organic phase was dried over anhydrous sodium sulfate for 2 h, filtered, and evaporated, evaporated, evaporated.A white solid was obtained in 6.8 g, yield: 87.1%.

According to the analysis of related databases, 287714-35-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Radioactive Medical Institute; Li Yiliang; Wei Huiqiang; Gao Jun; Bi Changfen; Ning Hongxin; Yu Jiang; Gou Wenfeng; Duan Yuqing; (35 pag.)CN109232541; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5018-41-7, name is 4-Amino-6-chloro-5-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 5018-41-7

6-(4-(1 -(2-(azetidin-1 -yl)ethyl)-4-(2-(thfluoromethyl)Dvhdin-4-yl)-1 H-imidazol-2- yl)piperidin-1 -yl)-5-methoxypyrimidin-4-amine (“1 15”) A reaction mixture of 6-Chloro-5-methoxy-pyrimidin-4-ylamine (45.00 mg; 0.28 mmol; 1 .00 eq.), 4-[1 -(2-Azetidin-1 -yl-ethyl)-2-piperidin-4-yl-1 H-imidazol-4-yl]-2- trifluoromethyl-pyridine hydrochloride (4) (148.13 mg; 0.28 mmol; 1 .00 eq.), and Cs2C03 (367.53 mg; 1 .13 mmol; 4.00 eq.) in DMSO 1 .0ml was stirred at 120C for 2days, purified by HPLC collected title compound 17mg. LC-MS: (M+1 = 503, obsd. = 503).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 5018-41-7, 4-Amino-6-chloro-5-methoxypyrimidine.

Reference:
Patent; MERCK PATENT GMBH; LAN, Ruoxi; HUCK, Bayard R.; CHEN, Xiaoling; XIAO, Yufang; DESELM, Lizbeth Celeste; QIU, Hui; NEAGU, Constantin; BANKSTON, Donald; JONES, Christopher Charles Victor; WO2013/40059; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1722-12-9 ,Some common heterocyclic compound, 1722-12-9, molecular formula is C4H3ClN2, 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 5 Synthesis of HK-9, HK-11, HK-13 and HK-15 The following describes the general synthesis of 2-(pyrrolidine-1-yl)pyrimidine (HK-9), 4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine, HK-11, 2-(piperidine-1-yl)pyrimidine (HK-13), 4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (HK-15), 5-benzyloxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 35), 5-benzyloxy-2-(piperidine-1-yl)pyrimidine (Compound 36), 5-benzyloxy-4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 37), and 5-benzyloxy-4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (Compound 38). Referring to the reaction scheme of , to 9.53 mL (116 mmol) pyrrolidine (29) in 400 mL of anhydrous THF was added 2.78 g of sodium hydride (116 mmol) and the mixture was refluxed for 0.5 hr. After cooling to r.t., 12 g (105 mmol) of 2-chloropyrimidine (33) was added dropwise and the mixture was refluxed for 2 days and then cooled in an ice bath. Water (200 mL) was then added to the cooled reaction mixture and the THF was removed in vacuo. The aqueous residue was extracted with CHCl3 and the combined CHCl3 extracts were washed with brine, dried over magnesium sulfate, and filtered. After removal of solvent in vacuo, the residue was purified by silica gel column chromatography using 20:1 hexanes:EtOAc as eluent. The product was then recrystallized from diethyl ether (Et2O) to give a 12.0 g (76%) of HK-9 as a yellow solid, mp 39.0-39.6 C. 1H NMR (CDCl3) delta 8.31 (d, J=4.88 Hz, 2H), 6.45 (t, J=4.88 Hz, 1H), 3.57 (t, J=4.4 Hz, 4H), 2.01-1.98 (m, 4H). Anal. Calcd for C8H11N3; C, 64.40; H, 7.43; N, 28.16. Found: C, 64.42; H, 7.53; N, 27.97.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1722-12-9, its application will become more common.

Reference:
Patent; KADOR, PETER F.; US2014/235858; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 23631-02-9, 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. 23631-02-9, name is 4-Chloro-N,N-dimethylpyrimidin-2-amine. A new synthetic method of this compound is introduced below.

A mixture of N-(cis-4-bromo-2-trifluoromethoxy-benzyl)-cyclohexane-1, 4- diamine obtained in step B of example 1 (466 mg), (4-chloro-pyrimidin-2-yl)-dimethyl- amine (200 mg), and BuOH (1 mL) was stirred at reflux for 13 hr. The mixture was poured into saturated aqueous NaHC03 and the aqueous) layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromttography (NH-silica gel, 20% EtOAc in) to give N4-(cis-4-{[4-bromo-2-(trifluoromethoxy) benzyl] arnino}-cyclohexyl)-Na, N2- dimethylpyrimidine-2, 4-diamine. To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure The residue was suspended in Et20 (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give N4-(cis-4-{ [4-bromo-2-(trifluoromethoxy) benzyl]-amino} cyclohexyl)-N2, N2- dimethylpyrimidine-2, 4-diamine dihydrochloride (294 mg). ESI MS m/e 488, M (free) + H+ ;’H NMR (300 MHz, CDCI3) 8 1.42-1. 67 (m, 2 H), 2.03- 2.39 (m, 6 H), 2. 79-3.38 (m, 7 H), 4.13-4. 36 (m, 3 H), 6.89-7. 00 (m, 1 H), 7.42-7. 46 (m, 1 H), 7.50-7. 57 (m, 1 H), 7. 90-8. 01 (m, 1 H), 8.12 (d, J= 8.4 Hz, 1 H), 8.90-9. 00 (m, 1 H), 9.98-10. 18 (m, 2 H), 12.21-12. 37 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23631-02-9, 4-Chloro-N,N-dimethylpyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 6299-25-8

Example 2C4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid; To a solution of diisopropylamine (20 mL, 142 mmol) in tetrahydrofuran (170 mL) at -78C was added n-butyl lithium (55.4 mL, 2.5M solution in hexane, 138 mmol). The mixture was stirred at -78C for 1 hour and was charged with a solution of the product of Example 2B (18 g, 92.3 mmol) in tetrahydrofuran (40 mL). After stirring at -78C for 3 hours, dry carbon dioxide was bubbled into the mixture for 30 minutes, followed by the addition of water at low temperature. The mixture was allowed to warm to ambient temperature and the mixture was adjusted to pH = 1 by addition of 2M hydrochloric acid. The mixture was extracted with ethyl acetate (3 x 300 mL) and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was washed with toluene to obtain the title compound. MS: 239 (M+H+).

The synthetic route of 6299-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; VASUDEVAN, Anil; PENNING, Thomas; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; WU, Fengchun; SHEN, Yan; LIU, Cuihua; ZOU, Zhenguang; WO2012/97478; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia