Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 3934-20-1, 2,4-Dichloropyrimidine, 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, Formula: C4H2Cl2N2, blongs to pyrimidines compound. Formula: C4H2Cl2N2

Example 90 Preparation of Intermediate 90 To a solution of 2,4-dichloropyrimidine (149 mg, 1 mmol) in THF (5 mL), tetrakis(triphenylphosphine)palladium (23 mg, 2 mol %) and 0.5M solution of phenylzinc bromide (2.1 mL, 1.05 mmol) in THF were added. The reaction mixture was stirred at 50 C. for overnight. Then it was added saturated ammonium chloride solution and extracted with EtOAc twice. The organic layers were combined, washed with water and dried (MgSO4). Filtration and concentration of solvent gave a yellow residue which was purified by Prep. HPLC to afford a yellowish oil as 2-chloro-4-phenyl-pyrimidine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3934-20-1, 2,4-Dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Sin, Ny; Good, Andrew Charles; Venables, Brian Lee; Scola, Paul Michael; Meanwell, Nicholas A.; US2006/183694; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22536-61-4, 2-Chloro-5-methylpyrimidine, 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, 22536-61-4, blongs to pyrimidines compound. HPLC of Formula: C5H5ClN2

A solution of 2-chloro-5-methylpyrimidine (500 g, 3889 mmol, 1.0 equiv) in DMF (5000 mL) was degassed with N2 for 20 mm and then dppf (108 g, 194 mmol, 0.05 equiv) and Pd2(dba)3 (178 g, 194 mmol, 0.05 equiv) were added to the reaction mixture. Zn(CN)2 (685 g, 5834 mmol, 1.5 equiv) was added, and the reaction mixture was heated at 100 C for 16 h. The reaction was quenched with water (5 L) and stirred for 10 mm. The reaction mixture was filtered through Celite brand filter aid pad. The filtrate was diluted with water (4 L) and extracted with EtOAc (2 x 4 L). The combined organic layers were washed with brine (4 L), dried over Na2SO4, filtered, and concentrated in vacuo to give the initial productwhich was further purified by column chromatography using silica gel (60-120 mesh) and0-10 % EtOAc in hexane to obtain Example 374.01 (330 g, 71 %) as an off white solid.1H NMR (400 MHz, DMSO-d6) oe 8.89 (s, 2H), 2.39 (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,22536-61-4, its application will become more common.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-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, 90349-23-8, blongs to pyrimidines compound. SDS of cas: 90349-23-8

To a stirred solution of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (50 mg, 0.262 mmol), 2-methyl-lH-l,3-benzodiazol-6-amine (57 mg, 0.314 mmol) and HATU (149 mg, 0.393 mmol) in DMF (1 mL) was added DIPEA (0.14 mL, 0.786 mmol), and the reaction mixture was stirred at room temperature for 16 hours until the reaction was complete. The suspension was diluted with H20 (3 mL), and the precipitated solid was collected by filtration, washed with minimum DCM and Et20, and purified by prep-HPLC (MeCN/10 mM NH4HCO3) to give the title compound (28 mg, 33%) as a white solid.XH NMR (400 MHz, DMSO-i/6) 5 12.16 (s, 1H), 10.18 (d, J= 31.2 Hz, 1H), 8.63 (s, 1H), 8.09 (d, J= 53.2 Hz, 1H), 7.49-7.16 (m, 3H), 2.78 (s, 3H), 2.72 (s, 3H), 2.49 (s, 3H). ES-MS m/z: 321.1 [M+H]+. LC-MS Purity (254 nm): 99%; tR= 1.46 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90349-23-8, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 16075-42-6, 2-Amino-4-(trifluoromethyl)pyrimidine, 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, name: 2-Amino-4-(trifluoromethyl)pyrimidine, blongs to pyrimidines compound. name: 2-Amino-4-(trifluoromethyl)pyrimidine

General procedure: Two mmol 5b1-5b20 was added to a dichloromethane solution containing 0.3 mL triethylamine at 0 C. Then 1.2 equiv. 3-chloropropionyl chloride was dissolved in dry dichloromethane, and the obtained mixture was slowly added to the aniline solution at 0 C. The reaction mixture was allowed to slowly warm up to room temperature, extracted with dichloromethane and finally washed with 2 M HCl. The organic phase was combined and dried with anhydrous MgSO4. Filtration and removal of the solvent under reduced pressure gave the crude product. The desired product was further purified by flash column chromatography with petroleum ether-EtOAc (20:1 to 10:1) to produce 6b1-6b20.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16075-42-6, 2-Amino-4-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Zhu, Kongkai; Song, Jia-Li; Tao, Hong-Rui; Cheng, Zhi-Qiang; Jiang, Cheng-Shi; Zhang, Hua; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3693 – 3699;,
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Pyrimidine – Wikipedia

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. 5750-74-3, name is 2,5-Dichloro-4-methoxypyrimidine. A new synthetic method of this compound is introduced below., Product Details of 5750-74-3

A solution of (2S,4R)-tert-butyl 4-amino-2-methylpyrrolidine-l-carboxylate (200 mg, 1.0 mmol), 2,5-dichloro-4-methoxypyrimidine (358 mg. 2.0 mmol) and K2C03 (226 mg, 2.0 mmol) in DMSO (10 mL) was stirred at RT for 2 hrs. The reaction mixture was diluted with water (30 mL) and extracted with EA (20 mL*3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE:EA = 1 : 1) to afford (2S,4R)-tert-butyl 4-((5-chloro-4- methoxypyrimidin-2-yl)amino)-2-methylpyrrolidine-l-carboxylate (100 mg, 30%) as a white solid. [M+H] Calc?d for CisH^ClN^s, 343.1; Found, 343.1

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, 5750-74-3, 2,5-Dichloro-4-methoxypyrimidine.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3764-01-0, 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 3764-01-0 as follows.

Under a nitrogen atmosphere, trichloropyrimidine (10 g, 54.5 mmol), phenylboronic acid (13.3 g, 109 mmol), palladium acetate (0.3 g, 1.37 mmol), triphenylphosphine (0.72 g, 2.73 mmol), dimethoxyethane (150 mL) and an aqueous solution of 2M sodium carbonate (170 mL) were added together in sequential order, and heated to reflux for eight hours. -After the reaction solution was cooled down to the room temperature, an organic phase was removed and an organic solvent was distilled away under reduced pressure. The obtained residue was refined by silica-gel column chromatography, whereby an intermediate 5-1 (9.2 g, a yield of 63%) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3764-01-0, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; Nishimura, Kazuki; Ogiwara, Toshinari; Hibino, Kumiko; Inoue, Tetsuya; Ito, Mitsunori; (130 pag.)US9711732; (2017); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 111196-81-7, 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 111196-81-7 as follows.

Step 1: l-(5-ethylpyrimidin-2-yl)piperidin To a solution of piperidin-4-ol (2.55 g, 25.2 mmol) in MeCN (50 mL) was added 2-chloro-5-ethylpyrimidine (3.00 g, 21.0 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (7 mL, 42.0 mmol) and the resulting reaction mixture was heated to 80C for 16 hrs. The mixture was diluted with water, extracted with EtOAc, washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified with column chromatography (CH2C12: EtOAc = 3:1 to 1:1) to afford the desired product (3.69 g, 85%) as a yellow solid.1H NMR (CDC13): delta 8.16 (2H, s), 4.37-4.42 (2H, m), 3.92-3.94 (1H, m), 3.24-3.30 (2H, m), 2.45 (2H, q, / = 7.6 Hz), 1.92-1.98(2H, m), 1.69 (1H, brs), 1.48-1.53 (2H, m), 1.19 (3H, t, / = 7.6 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111196-81-7, its application will become more common.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; ZHU, Yan; HU, Yuandong; WANG, Huting; LIU, Yuliang; LI, Jijun; SUN, Deguang; WANG, Zhe; WEI, Yongheng; WANG, Zanping; TANG, Guojing; JING, Lutao; WO2012/103806; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 611-08-5, 5-Nitrouracil, 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, name: 5-Nitrouracil, blongs to pyrimidines compound. name: 5-Nitrouracil

25 gm of 5-nitro uracil is suspended in 490 ml of phosphorous oxychloride for 10 minutes and diisopropyl ethylamine is slowly added to the suspension at room temp. The reaction suspension is refluxed at 130 oC for 3h. The solution is concentrated under reduced pressure to be a volume of 100 ml. Then the solution is added dropwise to 500 ml of ice water and stirred for 1h, and extracted with diethyl ether. The organic layer is washed with 500 ml of saturated ammonium chloride and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (ethyl acetate: Hexane=1:5) affords 16.8 gm of the title compound. White solid; mp:30-32 oC; IR (KBr): 1670, 1620, 1350, 785 cm-1; 1H NMR (400 MHz, CDCl3): delta 9.25 (s, 1H, H6) ppm; m/z=195(M+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,611-08-5, 5-Nitrouracil, and friends who are interested can also refer to it.

Reference:
Article; Sadanandam; Jyothi; Adharvana Chari; Das, Parthasarathi; Mukkanti; Tetrahedron Letters; vol. 52; 42; (2011); p. 5521 – 5524;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 7461-50-9, Adding some certain compound to certain chemical reactions, such as: 7461-50-9, name is 2-Chloropyrimidin-4-amine,molecular formula is C4H4ClN3, 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 7461-50-9.

A microwave reaction vessel was charged with 4-amino-2-chloropyrimidine (100 mg, 0.774 mmol, 1.0 eq), 2-methanesulfonyl-2-methylpropan-l -ol (353 mg, 2.33 mmol, 3.0 eq), and potassium carbonate (160.3 mg, 1.16 mmol, 1.5 eq) in propan-2-ol (1 mL). The reaction was stirred at room temperature for 1 min and heated under microwave irradiation at 200 C for 2.5 h (Biotage Initiator, maximum pressure set at 22 bar). The reaction mixture was cooled to room temperature and purified by chromatography on silica (solvent gradient: 0-10% 2M methanolic ammonia in ethyl acetate) to afford the title compound (163 mg, 86%). LCMS (ESI): [M+H]+ 246.3.

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. 7461-50-9, 2-Chloropyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; DIEDERICH, Francois; DOTSON, Jennafer; HANAN, Emily; HEFFRON, Timothy; LAINCHBURY, Michael; HEALD, Robert; SEWARD, Eileen M.; WO2014/210354; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C6H4ClN3

Preparation 1; The solution of 5-chloropyrazolo [ 1, 5-a] pyrimidine (200 mg) and trans-4-methoxycyclohexanamine (168 mg) in isopropylalcohol(2 ml) was refluxed for 3 hours. After cooling to ambient temperature, the reaction mixture was poured into water, then extracted with ethyl acetate . The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel EPO elupsilonting with chloroform/methanol ( 100 : 0 to 100:10) to give N- (trans-4-methoxycyclohexyl)pyrazolo [1, 5-a] pyrimidin-5- amine (70 mg) .1H-NMR (DMSO-d6) 5:1.13-1.34 (4H,m) ,1-91-2.08 (4H,m) , 3.09-3.20 ( IH, m) ,3.33 (3H,s) , 3.70-3.86 (lH,m) ,5.95 (IH, d, J=2. OHz) ,6.19 (IH , d, J=7.6Hz) , 7.26(lH,d, J=7.4Hz) ,7.74 ( IH, d, J=2. OHz) , 8.41 (IH, d , J=7.6 Hz) . MS:247 (MH-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, 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/13673; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia