Tag: M.W:200-300

Synthetic Route of 6299-85-0, 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. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Preparation of compound 47a: methyl 2-chloro-6-cyclopropylpyrimidine-4- carboxylateIn a 5 mL glass microwave tube methyl 2,4-dichloropyrimidine-6-carboxylate (621 mg, 3.00 mmol) (Astatech Inc.) and Amphos (53.1 mg, 0.075 mmol) were treated with cyclopropylzinc(II) bromide (Rieke, 0.5 M in THF) (1.2 mL, 6.00 mmol) via syringe under an atmosphere of argon. The solution was then heated in the microwave at 80 C for 20 min. The mixture was treated with EtOAc and IN NaOH resulting in a white suspension as the zinc hydroxide salts precipitated out. The suspension was extracted with EtOAc (50 mL) a second time and washed with brine and dried over Na2S04, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 100% DCM) to give methyl 2-chloro-6-cyclopropylpyrimidine-4-carboxylate (254 mg, 40% ) as a clear, colorless, viscous oil. MS (ESI, pos. ion) m/z: 213.1 (M+l). .H NMR (400 MHz, CDCh) delta ppm 7.77 (1 H, s), 3.99 – 4.04 (3 H, m), 2.06 – 2.15 (1 H, m), 1.20 – 1.31 (4 H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6299-85-0, its application will become more common.

Reference:
Patent; AMGEN INC.; WANG, Hui-Ling; CEE, Victor, C.; HERBERICH, Bradley, J.; JACKSON, Claire, L., M.; LANMAN, Brian, Alan; NIXEY, Thomas; PETTUS, Liping, H.; REED, Anthony, B.; WU, Bin; WURZ, Ryan; TASKER, Andrew; WO2012/129338; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1224944-51-7, 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. 1224944-51-7, name is Methyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C8H6ClN3O2, 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.

A microwave vial was charged with methyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (500 mg, 2.36 mmol), tert-butyl N-[(1S,2R)-2-aminocyclohexyl]carbamate (506 mg, 2.36 mmol), and methanol (4.7 mL). The vial was sealed and stirred at 90 C for 30 min in the microwave, resulting in a suspension. The reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography (0-100% isopropyl acetate/heptane) to afford methyl 5- [[(1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl]amino]pyrazolo[1,5-a]pyrimidine-3- carboxylate (420.2 mg, 1.08 mmol, 46% yield) as a white solid. MS: m/z = 390 (M+1).

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 1224944-51-7, Methyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 180869-36-7, Adding some certain compound to certain chemical reactions, such as: 180869-36-7, name is 4-(Dimethoxymethyl)-2-(methylthio)pyrimidine,molecular formula is C8H12N2O2S, 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 180869-36-7.

Example 29A (14.6 g) was dissolved in methanol (122 mL) and water (122 mL) and the stirring mixture was cooled with an ice bath then oxone (potassium peroxomonosulfate) (67.2 g) was added portionwise over 15 minutes. The resulting mixture was stirred at 0 C for 3 hours, and the cooling bath was removed to allow for the reaction to stir at room temperature for an additional 2 hours. The mixture was concentrated to remove most of the methanol and the remaining aqueous mixture was filtered and washed with ~200 mL of methylene chloride. The biphasic mixture was poured into a separatory funnel, the organic layer was removed and the aqueous layer was washed with one portion of methylene chloride. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated onto silica gel. Purification by flash chromatography on a CombiFlash Teledyne Isco system using a Teledyne Isco RediSep Rf gold 330 g silica gel column (eluting 50-100% ethyl acetate/heptane) afforded the title compound. MS (APCI) m/z 233.3 (M+H)+.

According to the analysis of related databases, 180869-36-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; BRAJE, Wilfried; DOHERTY, George; JANTOS, Katja; JI, Cheng; JUDD, Andrew; KUNZER, Aaron; MASTRACCHIO, Anthony; SONG, Xiaohong; SOUERS, Andrew; SULLIVAN, Gerard; TAO, Zhi-Fu; LAI, Chunqui; KLING, Andreas; POHLKI, Frauke; TESKE, Jessc; WENDT, Michael; BRADY, Patrick; WANG, Xilu; PENNING, Thomas; MICHAELIDES, Michael; (448 pag.)WO2019/35927; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.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, molecular weight is 298.3, as common compound, the synthetic route is as follows.HPLC of Formula: C15H14N4O3

To a solution of pemetrexed-fragment 2 (60mg, 0.2mmol) and amine SDC-TRAP-0004 (82mg, 0.2mmol) in anhydrous DMF (3 mL) was added EDC (60mg, 0.3mmol). The reaction mixture was stirred at room temperature for 18h. The reaction mixture was then diluted with water (5 mL) and extracted with ethyl acetate (lOOmL). The organic phase was dried with sodium sulfate, filtered and evaporated, followed by flash chromatography (hexane-ethyl acetate 1:1 and ethyl acetate-methanol 98:2) to give SDC-TRAP-0019 (95mg, 70%) as a white solid 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)- N-(2-(5-(3-(2,4-dihydroxy-5-isopropylphenyl)-5-hydroxy-4H-1,2,4-triazol-4-yl)-1H-indol- 1-yl)ethyl)-N-methylbenzamide 1H NMR (400 MHz, DMSO-d6) : 11.86 (s, 111); 10.61(s, 111); 10.14(s,1H);9.51 (s, 111); 9.47 (s, 111); 7.59-7.45 (m, 211); 7.28-6.96 (m, 511); 6.72 (m, 211);6.47(s,1H); 6.32 (s, 111); 6.24 (s, 111); 6.00( bs, 211); 4.46-4.28 (m,2H);3.75-3.49(m,2H); 2.96 -2.80(m, 511); 2.61(s, 311); 0.81 (d, J = 6.9 Hz, 611).ESMS calculated for C371137N905: 687.29; Found: 688.2 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; CHIMMANAMADA, Dinesh, U.; YING, Weiwen; (368 pag.)WO2015/143004; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 353272-15-8, 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.353272-15-8, name is 6-Chloro-5-iodopyrimidin-4-amine, molecular formula is C4H3ClIN3, molecular weight is 255.4442, as common compound, the synthetic route is as follows.

To a mixture of 6-chloro-5-iodopyrimidin-4-am.ine (500 mg, 0.196 mmol), Pd(PPh3)2Cl2 (69 mg, 0.10 mmol ) and Cul (19 mg, 0.10 mmol) under 2 atmosphere were added a solution of etiiynyltrimethylsilane (1 ,38 mL, 9.79 mmol) in DMF (1.5 mL) and a solution triethylamine (0.54 mL, 3.91 mmol) in DMF (1.5 mL), The resulted mixture was heated to 47 C and stirred further for 2 hours. The mixture was diluted with EtOAc (30 mL), and the resulted mixture was washed with water (20 mL x 2) and brine (20 mL). The separated organic phase was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) ::: 10/1) to give the title compound as a brown solid (442 mg, yield 100%). MS (ESI, pos. ion) m/z: 226.0 [M+H]+; NMR (400 MHz, CDCb) delta (ppm): 8.31 (s, 1H), 5.62 (s, 2H), 0.31 (s, 9H).

Statistics shows that 353272-15-8 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-5-iodopyrimidin-4-amine.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 90914-41-3, 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. 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

A microwave tube containing 19.3 mg of 5-phenyl-o-anisidine (0.097 mmol), 25.1 mg of 3-bromo-4-chloro-lH-pyrazolo[3,4-d]pyrimidine (0.11 mmol), 9.2 mu^ of glacial acetic acid (0.16 mmol) and 1 mL of n-butanol with a stir bar was capped and heated to 130C for 15 min in a microwave reactor. The reaction was cooled and concentrated by rotary evaporation. The residue was recrystallized in ethanol to give 30.7 mg of crude 4 as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SHEN, Weijun; NOVOTNY, Christopher; SHOKAT, Kevan, M.; (490 pag.)WO2017/184775; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 90213-67-5, Adding some certain compound to certain chemical reactions, such as: 90213-67-5, name is 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C7H5Cl2N3, 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 90213-67-5.

General procedure: A solution of 1 (400 mg, 1.98 mmol) in anhydrous toluene (10 mL)was flushed with Ar and Pd(PPh3)2Cl2 (14.0 mg, 0.02 mmol), AsPh3(24.5 mg, 0.08 mmol) and the corresponding (arylethynyl)tributylstannane(2.38 mmol) were added. The mixture was stirred under Ar at 80 C for 2 h. After cooling, the mixture was poured into aq K2CO3 solution (0.5 M, 25 mL) containing CsF (50 mg), stirred for 30 min and then extracted with CHCl3. The extract was dried over Na2SO4, filtered and the CHCl3 removed on a rotary evaporator. The residue was purified by column chromatography (CHCl3) to afford 2a-h.

According to the analysis of related databases, 90213-67-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bucevicius, Jonas; Tumkevicius, Sigitas; Synthesis; vol. 47; 14; (2015); p. 2100 – 2112;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1032650-41-1 ,Some common heterocyclic compound, 1032650-41-1, molecular formula is C6H3BrClN3, 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.

Step 4: Preparation of 7-bromo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine N,N-dimethylformamide (10 mL) and NaH (36 mg) were added to 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (147 mg), followed by stirring for 30 mins. Subsequently, methyl iodide was added thereto, and the mixture was heated under stirring at 50C for 2 hrs. Upon completion of the reaction, ethyl acetate was added thereto, and the mixture was washed with water. The resulting compound was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): delta 8.68(s, 1H), 8.22(s, 1H), 4.11 (s, 3H).

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. 1032650-41-1, 7-Bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hanmi Pharmaceutical Co., Ltd.; PARK, Chul Hyun; KIM, Won Jeoung; JUNG, Young Hee; KIM, Nam Du; CHANG, Young Kil; KIM, Maeng Sup; EP2738174; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1224944-77-7 , The common heterocyclic compound, 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H8ClN3O2, 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.

General procedure: To a solution of 0.25 g (0.92 mmol) of compound 7-3 dihydrochloride salt in 23 mL of DMSO was added 0.19 g (0.86 mmol) of ethyl 6-chloroimidazo[1 ,2-b]pyridazine-3-carboxylate and 0.40 g (6.8 mmol) of KF. The mixture was stirred at 180 C for 2 h and cooled down to rt. It was diluted with 250 mL of water and extracted with 250 mL of ethyl acetate. The combined organic extracts were washed with brine and dried over anhydrous Na2S04. After filtration, the filtrate was concentrated to afford a residue, which was purified by Prep-TLC (ethyl acetate / petroleum ether = 1 :1 ) to afford compound 7-4. LC-MS: m/e = 386 [M+H]+.

The synthetic route of 1224944-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANGEX PHARMACEUTICAL, INC.; WU, Wen-Lian; YANG, Zhiqiang; LEE, Francis; TAN, John Qiang; (112 pag.)WO2019/94143; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1207518-63-5, Methyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, 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, 1207518-63-5, blongs to pyrimidines compound. name: Methyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Example 44; (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol (44.1); To a suspension of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid methyl ester (example 43) (1.0 g, 4.716 mmol) in dichloromethane (60.0 mL) cooled to -780C, is added a solution of DIBAL-H (1.0 M in toluene, 14.15 mL, 14.15 mmol) dropwise. The resulting solution is stirred at -780C for 2 h and then at room temperature until TLC analysis indicates complete consumption of intermediate 43.2 (3 h). The reaction is quenched with aqueous NH4CI and stirred for 10 min. The salts separated are filtered off and the filtrate is washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue is impregnated over silica gel using methanol and the impregnated silica gel is loaded onto a silica gel column. Elution with a solvent gradient of CH2CI2 : MeOH = 90: 10 followed by evaporation of the eluted solvent gives intermediate 44.1 as a brown solid. 1H NMR (400 MHz, CDCI3): delta 12.35 (brs, 1 H), 8.54 (s, 1 H), 7.54 (s, 1 H), 5.01 (t, J = 5.07 Hz, 1 H), 4.75 (d, J = 5.07 Hz, 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,1207518-63-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; CHEN, Yen-Liang; DURAISWAMY, Jeyaraj; KONDREDDI, Ravinder Reddy; YIN, Zheng; WO2010/15637; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia