Tag: M.W:100-200

Reference of 69034-12-4, Adding some certain compound to certain chemical reactions, such as: 69034-12-4, name is 2-Chloro-5-(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 69034-12-4.

Example 1.37: Preparation of 4-((lr,4r)-4-((l-(5-(Trifluoromethyl)pyrimidin-2-yl)piperidin- 4-yl)methoxy)cyclohexyl)nicotinonitrile (Compound 59).; A mixture of 4-((lr,4r)-4-(piperidin-4-ylmethoxy)cyclohexyl)nicotinonitriledihydrochloride (27 mg, 72.52 muetaiotaomicron), 2-chloro-5-(trifluoromethyl)pyrimidine (0.03 ml, 0.164 mmol), and potassium carbonate (50 mg, 0.362 mmol) in 1 ml iPrOH was heated under micorwave irradiation at 85C for 2 h. Mixture was purified by HPLC (CH3CN/H20 gradient + 0.1% TFA). Fractions containing desired product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give 4-((lr,4r)-4-((l-(5-(trifluoromethyl)pyrimidin-2-yl)piperidin-4- yl)methoxy)cyclohexyl)nicotinonitrile (14.6 mg, 32.77 muetaiotaomicron, 45.2 %) as a white solid. Exact mass calculated for C23H26F3N50: 445.21, found: LCMS m/z = 446.4 (M+H+); lU NMR (400 MHz, CDC13) delta ppm 1.17-1.28 (m, 2H), 1.41-1.62 (m, 4H), 1.85-2.04 (m, 5H), 2.18-2.24 (m, 2H), 2.90-2.99 (m, 3H), 3.26-3.33 (m, 1H), 3.38 (d, = 6.0 Hz, 2H), 4.84-4.90 (m, 2H), 7.28 (d, = 5.3 Hz, 1H), 8.47 (s, 2H), 8.80 (d, = 5.3 Hz, 1H), 8.81 (s, 1H).

According to the analysis of related databases, 69034-12-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 39906-04-2, 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. 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine, molecular formula is C5H5Cl2N3, 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.

General procedure: A microwave vial was charged with 3′-aminoacetanilide 29 (300 mg, 2.0 mmol), 5-amino-4,6-dichloropyrimidine (10) (328 mg, 2.0 mmol), acetic acid (100 muL) and isobutanol (10 mL) and was irradiated at 150 C for 30 min. After cooling, dichloromethane was added (20 mL) and the crude reaction mixture was washed with saturated aqueous NaHCO3 (20 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by flash chromatography (dichloromethane:methanol).Yield: 300 mg (54%).

According to the analysis of related databases, 39906-04-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Aguado, Leire; Canela, Maria-Dolores; Thibaut, Hendrik Jan; Priego, Eva-Maria; Camarasa, Maria-Jose; Leyssen, Pieter; Neyts, Johan; Perez-Perez, Maria-Jesus; European Journal of Medicinal Chemistry; vol. 49; (2012); p. 279 – 288;,
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. 149849-94-5, name is Methyl 2-chloropyrimidine-4-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Methyl 2-chloropyrimidine-4-carboxylate

A solution of 5-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-4-(trifluoromethyl)-2-[[2-(trimethylsilyl)ethoxy]methyl]-2,3-dihydropyridazin-3-one (500 mg, 1.27 mmol, 1.00 equiv), (Pd(allyl)C)2 (47 mg, 0.10 equiv), Rockphos (60 mg, 0.10 equiv), Cs2CO3 (829 mg, 2.54 mmol, 2.00 equiv), methyl 2-chloropyrimidine-4-carboxylate (547 mg, 3.17 mmol, 2.50 equiv) in toluene (10 mL) under nitrogen atmosphere was stirred overnight at 85 C. The solvent was concentrated under vacuum and the residue was applied onto a silica gel column eluting with EtOAc/petroleum ether (3/7) to afford 425 mg (63%) of the title compound as a yellow solid. LCMS (ESI, m/z): 530.20 [M+H]+.

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, 149849-94-5, Methyl 2-chloropyrimidine-4-carboxylate.

Reference:
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 45695-56-5, 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. 45695-56-5, name is Pyrimidine-2-carboximidamide. A new synthetic method of this compound is introduced below.

Compound 159 Enantiomers of racemic mixture 159: 159a and 159b A mixture of compound 129 (4 g crude), 2-pyrimidinecarboximidamide (2.35 g, 19.2 mmol) and 1 , 4-dioxane (25 mL) was stirred at 40C for 72 hours and allowed to reach room temperature. The reaction mixture was evaporated to dryness to afford a brown residue. This residue and phosphorus oxychloride (20.9 mL, 225 mmol) were stirred at 120C for 45 minutes in a round bottomed flask. The reaction mixture was concentrated in vacuo at 50C and co evaporated with toluene (2 x 100 mL). The residue was dissolved in dichloromethane (250 mL) and washed with saturated aqueous sodium bicarbonate (100 mL), dried (Na2S04) and evaporated to afford a dark brown residue. This residue was purified using silica gel column chromatography (dichloromethane in heptane from 50 to 100%) to methyl 6-chloro-4-(3,4- difluorophenyl)-4-methyl-2-(pyrimidin-2-yl)- 1 ,4-dihy dropyrimidine-5 -carboxylate (1800 mg) as light yellow solid. A solution of methyl 6-chloro-4-(3,4-difluorophenyl)- 4-methyl-2-(pyrimidin-2-yl)-l,4-dihy dropyrimidine-5 -carboxylate (900 mg) in 1 , 4- dioxane (10 mL) in a microwave-vial was stirred and purged with nitrogen for 10 minutes. Then tetramethyltin (494 mu, 3.56 mmol) was added followed by bis (tri-t- butylphosphine) palladium (0) (243 mg, 0.475 mmol) and the vial was flushed with nitrogen and capped. The reaction mixture was heated under microwave irradiation at 140C for 30 minutes and allowed to reach room temperature. The reaction mixture was stirred and purged with nitrogen for 10 minutes, bis(tri-t-butylphosphine) palladium (0) (121 mg, 0.238 mmol) was added and the vial was flushed with nitrogen and capped. The reaction mixture was heated by microwave irradiation at 145C for 30 minutes and allowed to reach room temperature. The reaction mixture was concentrated in vacuo. The obtained residue was mixed with dichloromethane (100 mL) and the orange precipitate was filtered off. The filtrate was washed with water (2 x 20 mL), dried (Na2S04) and concentrated in vacuo. The obtained residue was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 100%) to afford compound 159 as yellow sticky oil. Method A; Rt: 0.86 m/z; 359.2 (M+H)+ Exact mass: 358.1.Racemix mixture 159 was purified by Prep SFC (Stationary phase: Chiralpak Diacel AD 30 x 250 mm), Mobile phase: C02, Ethanol), yielding compound 159a and 159b as yellow powders. Columns: AD-H 250 mm x 4.6 mm; Flow: 3 ml/min; Mobile phase: 10 % EtOH (containing 0.2% iPrNH2) hold 15.00 min; Temperature: 30C; compound 159a: Rt (3.2 min), compound 159b Rt (4.5 min). 1H NMR (360 MHz, CHLOROFORM- , tautomeric mixture (-9/1), main isomer desribed) delta ppm 1.96 (s, 3 H), 2.34 (s, 3 H), 3.49 (s, 3 H), 7.04 (dt, J=10.0, 8.0 Hz, 1 H), 7.19 – 7.24 (m, 1 H), 7.30 (ddd, J=12.0, 8.0, 3.0 Hz, 1 H), 7.40 (t, J=5.0 Hz, 1 H), 8.41 (br. s., 1 H), 8.86 (d, J=5.0 Hz, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,45695-56-5, its application will become more common.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2013/102655; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 149849-92-3, 2-Chloropyrimidine-4-carboxylic acid, 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, Quality Control of 2-Chloropyrimidine-4-carboxylic acid, blongs to pyrimidines compound. Quality Control of 2-Chloropyrimidine-4-carboxylic acid

In a 100 mL flask was 2-chloropyrimidine-4-carboxylic acid (216 mg, 1.362 mmol) and 6-fluoro-4-(2-vinylmorpholino)pyridin-3-amine (304 mg, 1.362 mmol) in Ethyl acetate (3 mL) to give a tan solution. Hunig’s base (0.713 mL, 4.09 mmol) and 1- propanephosphonic acid cyclic anhydride (2.432 mL, 4.09 mmol) were added. The mixture was stirred at rt over the weekend for 66 h. LCMS showed conversion to the desired product. The mixture was basified with IN NaOH and diluted with EtOAc and water. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried and concentrated to afford the desired product (459 mg, 93%) as a tan oil/solid: 1H NMR (400 MHz, Chloroform-d) delta 10.51 (s, 1H), 9.24 (d, J = 0.7 Hz, 1H), 8.93 (d, J = 4.9 Hz, 1H), 8.13 (d, J = 4.9 Hz, 1H), 6.64 (d, J = 1.9 Hz, 1H), 5.51 (ddd, J = 17.8, 10.3, 7.7 Hz, 1H), 5.19 – 5.09 (m, 2H), 4.09 – 3.96 (m, 3H), 3.75 (td, J = 7.8, 2.9 Hz, 1H), 3.67 (dd, J = 11.2, 8.0 Hz, 1H), 3.11 (dt, J = 12.1, 3.1 Hz, 1H), 2.82 (ddd, J = 12.2, 9.1, 3.1 Hz, 1H); 19F NMR (376 MHz, Chloroform-d) delta -69.23; MS (ESI) (m/z): 364.2 (M+H)+.

The synthetic route of 149849-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; SIVAPRAKASAM, Prasanna; DUBOWCHIK, Gene M.; MACOR, John E.; (45 pag.)WO2018/98413; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-63-6, 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. 22536-63-6, name is 2-Chloro-4-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

To a solution of cis-1-(3-methoxyphenyl)-4-piperazin-1-ylcyclohexanecarbonitrile dihydrochloride (50 mg, 0.134 mmol), triethylamine (0.0654 ml, 0.469 mmol) and potassium carbonate (92.6 mg, 0.670 mmol) in N,N-dimethylformamide (DMF, 1.5 mL), 2-chloro-4-methoxypyrimidine (29.1 mg, 0.201 mmol) was added at room temperature, and then the mixture was heated to 70C and stirred for 5 hours. Water was added thereto to quench the reaction, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water twice, dried over anhydrous magnesium sulfate, filtrated, and the solvent was removed from the filtrate in vacuo. The residue was purified by silica gel chromatography to give 39.3 mg of the title compound as a white crystal. High-performance liquid chromatography/mass spectrometry m/z 408.4 (M+H) Retention time: 2.36 min.

According to the analysis of related databases, 22536-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1679069; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 89793-12-4, 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. 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

Step 1: A mixture of ethyl 2-chloropyrimidine-5-carboxylate (1.86 g, 10 mmol), compound 1 (4-amino-l-Boc-piperidine, 3.00 g, 15 mmol), and NEt3 (3.0 g, 30 mmol) in 1,4-dioxane (20 mL) was stirred at 95°C overnight. The mixture was concentrated, and EA (60mL) and aqueous citric acid (60 mL) were added to the mixture followed by stirring the mixture for 30 min. The organic layer was collected, dried and concentrated to get compound 2 (3.4 g, yield: 97percent) as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89793-12-4, Ethyl 2-chloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; SHEARSTONE, Jeffrey, R.; JARPE, Matthew, B.; (152 pag.)WO2016/57779; (2016); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 46155-89-9, 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 46155-89-9, name is 1,3-Dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 111 5-[4-(4-Chlorobenzoyl)benzyl]-1,3-dimethylpyrrolo [3,2-d]pyrimidine-2,4-dione To a solution of 1,3-dimethylpyrrolo[3,2-d]-pyrimidine-2,4-dione (0.402 g, 2.24 mmol) and 4-(4-chlorobenzoyl) benzyl bromide (1.20 g, 3.88 mmol) in DMF (5 ml) was added potassium carbonate (0.73 g, 5.28 mmol) and the mixture was stirred at 60 C. for 2 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developer: isopropyl ether: ethyl acetate: methylene chloride=2:1:1) and recrystallized from ethyl acetate to provide colorless needles. 0.360 g (39%) 1 H-NMR (CDCl3) delta: 3.40(3H,s), 3.49(3H,s), 5.66(2H,s), 6.00(1H,d,J=3.0 Hz), 7.01(1H,d,J=3.0 Hz), 7.29(2H,d,J=8.6 Hz), 7.45(2H,d,J=8.6 Hz), 7.72(2H,d,J=8.6 Hz),,7.73(2H,d,J=8.6 Hz). IR (KBr): 1693, 1653, 1549, 1466, 1434, 1406, 1267, 1065, 1016, 962, 922, 856, 744, 669, 503 cm-1.

According to the analysis of related databases, 46155-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5753664; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 14080-23-0, Adding some certain compound to certain chemical reactions, such as: 14080-23-0, name is 2-Cyanopyrimidine,molecular formula is C5H3N3, 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 14080-23-0.

To the flask was added 0.10g of 2cyanopyrimidine,12% by mass aqueous sodium hydroxide solution 13mL was stirred at 70 30 minutes. Of 1N dilutehydrochloric acid to pH ~ 3 by adding little by little and, by concentration of the resulting organic layer was extracted three times with 10mL of ethyl acetate, to give0.10g of Compound A218

According to the analysis of related databases, 14080-23-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG CHEMICAL CO., LTD; PARK, JONG HO; SAH, KONG CHUN; KIM, SUNG HYUN; BAEK, GYUNG LIM; RYU, CHANG HYUN; (91 pag.)KR2015/128789; (2015); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3680-69-1, 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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, 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.

Step 1To a solution of 4-chloro-7H-pyrro]o[2,3-d]pyrimidine (8.0 g , 52.32 mmol, 1.0 eq) in DMF (40 raL), NiS ( 15.7g , 57.55 mmol, 1.1 eq) was added at 0 C. The reaction mixture was stirred overnight at room temperature. Water (40 rnL) was added to the reaction mixture, extracted with EtOAc. The organic layer was dried over Na2S04 and concentrated under vacuum to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (14.6 g, 100 % in yield).

According to the analysis of related databases, 3680-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; WO2012/158795; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia