Month: April 2021

Electric Literature of 58347-49-2, 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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]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.

EXAMPLE 1 Preparation of 7-(3,5-di-t-butyl-4-hydroxyphenyl)-aminopyrazolo[1,5-a]pyrimidine: A suspension of 7-chloropyrazolo[1,5-a]pyrimidine (1.0 g), 3,5-di-t-butyl-4-hydroxyaniline hydrochloride (1.8 g) and diethylaniline (2.3 ml) in toluene (50 ml) is heated at 120 C. for 30 minutes. After cooling, the solvent is distilled off, and the residue is purified by silica gel column chromatography (solvent; CHCl3) to give 7-(3,5-di-t-butyl-4-hydroxyphenyl)aminopyrazolo[1,5-a]pyrimidine (890 mg) as colorless crystal. M.p. 264-266 C. (decomposed) 1 H-NMR (CDCl3): delta 1.48 (s, 18H), 5.63 (s, 1H), 5.92 (s, 1H), 6.55 (d, J=2.3 Hz, 1H), 7.47 (s, 2H), 8.14 (d, J=2.3 Hz, 1H)

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 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; Otsuka Pharmaceutical Factory, Inc.; US5688949; (1997); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol, molecular formula is C4H6N4S, 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. name: 4,6-Diaminopyrimidine-2-thiol

Potassium hydroxide (88.8 g, 1.58 mol) and 4,6-diamino-2-mercaptopyrimidine (45.0 g, 316 mmol) were sequentially added to 230 ml of water and heated at 85 C. for 2 h.Add 220 ml of methanol, 1-bromo-3,3,3-trifluoropropane (280 g, 1.58 mol) and KI(2.63 g, 15.8 mmol), continued stirring at 60 C for 24 h. The reaction solution was concentrated under reduced pressure.After cooling to room temperature, the filter cake was dried to obtain 71.6 g of a yellow solid with a yield of 95%.

With the rapid development of chemical substances, we look forward to future research findings about 1004-39-3.

Reference:
Patent; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Jianqi; Lu Kuanying; Ma Zhilong; Jin Xunqi; Zhou Chao; (21 pag.)CN107973832; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 62802-42-0, Adding some certain compound to certain chemical reactions, such as: 62802-42-0, name is 2-Chloro-5-fluoropyrimidine,molecular formula is C4H2ClFN2, 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 62802-42-0.

Preparation 152 N-[(4aR,7aR)-6-(5-Fluoropyrimidin-2-yl)-7a-isothiazol-5-yl-4,4-a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide 5-Fluoro-2-chloropyrimidine (58 mL, 608.3 mol), and diisopropylethylamine (227 mL 1.30 mol, 227.3 mL) is added to N-[(4aR,7aR)-7a-isothiazol-5-yl-4-a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-6-ium-2-yl]benzamide chloride (174.2 g, 434.5 mol), in N-methylpyrrolidone (1.4 L) at 22 C. and stirred. The reaction is heated at 100 C. for 4 hours and then cooled to room temperature. The crude mixture is added to water (14 L) and then stirred 1 hour. A white solid is collected by filtration and dried under vacuum to constant weight. The crude product is purified by silica gel chromatography, eluting with ethyl acetate: methylene chloride (3/1) to give the title compound (139 g, 72%). ES/MS (m/e): 441.0 (M+H).

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. 62802-42-0, 2-Chloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; BECK, James Peter; GREEN, Steven James; LOPEZ, Jose Eduardo; MATHES, Brian Michael; MERGOTT, Dustin James; PORTER, Warren Jaye; RANKOVIC, Zoran; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR, Leonard Larry; US2013/261111; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4316-98-7, 6-Chloro-4,5-diaminopyrimidine, 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, Application In Synthesis of 6-Chloro-4,5-diaminopyrimidine, blongs to pyrimidines compound. Application In Synthesis of 6-Chloro-4,5-diaminopyrimidine

1.6 g of the 2-(N-methylmethylsulfonamide)nicotinic acid obtained in this way are suspended in 10 ml of dichloromethane, and 0.6 ml of thionyl chloride is added dropwise. This suspension is stirred at 40 C. for 3 h, and, immediately after addition of a few drops of DMF, 3 is reacted further with 1 g of 6-chloropyrimidine-4,5-diamine at RT for 16 h. Removal of the solvent gives a 1:3 mixture of 2.3 g of the regioisomers 4, which are immediately reacted further in 30 ml of POCl3 at 50 C. in 48 h to give 5. Chromatography with dichloromethane/methanol=100:0->90:10 gives 810 mg of a colourless solid; LCMS: 339.0 (M+H), RT. 1.341 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-98-7, 6-Chloro-4,5-diaminopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; Heinrich, Timo; Rohdich, Felix; Esdar, Christina; Krier, Mireille; Greiner, Hartmut; US2015/218155; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5750-76-5, 2,4,5-Trichloropyrimidine, 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, 5750-76-5, blongs to pyrimidines compound. Computed Properties of C4HCl3N2

To a 250 mL round bottom flask equipped with a stir bar was added 1 g 5-chloro- 2,4-dichloro- pyrimidine, and l5mL of diethyl ether. The mixture was cooled to 0C inan ice bath and then 1 equivalent of sodium methoxide in methanol (prepared from reacting 120 mg of sodium with 4 mL of methanol at room temperature) was slowly added. The reaction was stirred over night at room temperature and checked by LCMS. The white precipitate was filtered and the solid washed with cold methanol. After drying, 0.98 g of pure 2,5-dichloro-4-methoxypyrimidine was obtained and this material wasused without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5750-76-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; CHAMBERS, Mark; CHAN, Bryan K.; ESTRADA, Anthony; SWEENEY, Zachary Kevin; WO2013/79495; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 955368-90-8 , The common heterocyclic compound, 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, molecular formula is C9H10N4OS, 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.

Into a 25 mL microwave vial was added 2-allyl-6-(methylthio)-1H-pyrazolo[3,4- d]pyrimidin-3(2H)-one (275 mg, 1.235 mmol) (obtained according to EP2213673B1, Production Example 1, p37), [(5-bromopyridin-3-yl)imino]dimethyl-A6-sulfanon (400 mg, 1.61 mmol), potassium carbonate (239 mg, 1.73 mmol) and dioxane (5 mL). The resultant suspension was degassed (bubbling of N2) and copper (I) iodide (235 mg, 1.235 mmol) was added followed by N1,N2-dimethylethane-1,2-diamine (0.133 mL,1.24 mmol). The vial was capped and the reaction mixture was stirred at 95 00 overnight. After cooling to RT the reaction mixture was transferred to a separation funnel, NH4OH (aq, 20 mL) was added and the resulting mixture was extracted with EtOAc (3 x 30 mL). The organic phases were combined, dried and evaporated under vacuum. The residue was purified using flash chromatography (0-15% MeOH in EtOAc). The product containing fractions were concentrated to give the title compound (60 mg, 12.44 % yield) as an yellowish oil that solidified upon storage. LCMS (Method C): RT = 0.99 mi mlz = 391 [M+H].1H NMR (300 MHz, ODd3) O 9.21 (5, 1H), 8.64 (5, 1H), 8.57 (5, 1H), 8.12 (5, 1H),5.70-5.41 (m, 1H), 5.17 (t, J = 5.1 Hz, 1H), 4.96 (d, J = 17.0 Hz, 2H), 4.53 (d, J = 6.0 Hz, 2H), 3.31 (5, 6H), 2.53 (5, 3H)

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BURKAMP, Frank; ROUNTREE, James Samuel Shane; TREDER, Adam Piotr; (155 pag.)WO2018/11569; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 63558-65-6, Adding some certain compound to certain chemical reactions, such as: 63558-65-6, name is 4-Chloro-5-iodopyrimidine,molecular formula is C4H2ClIN2, 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 63558-65-6.

Preparation 57A: 5-Iodo-4-(2H-l,2, -triazol-2-yl)pyrimidine[00244] To a solution of lH-l,2,3-triazole (63.2 mg, 0.915 mmol) in THF (Volume: 241 1 ??), was added portion wise at 0 C, NaH (39.9 mg, 0.998 mmol). The reaction mixture was stirred at that temperature for 30 min, then 4-chloro-5-iodopyrimidine (200 mg, 0.832 mmol) was added. The reaction mixture was allowed to warm to room temperature. To this solution was added saturated aqueous NH4C1 and the mixture was allowed to stir for 5 min at which time it was diluted with ethyl acetate and extracted 2X. The combined organics were washed with brine IX. The organics were dried overNa2S04, filtered and concentrated in vacuo to afford the title compound (90 mg, 40%).

According to the analysis of related databases, 63558-65-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3177-20-6, Methyl 2,4-dichloropyrimidine-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, COA of Formula: C6H4Cl2N2O2, blongs to pyrimidines compound. COA of Formula: C6H4Cl2N2O2

To a solution of 2,4-dichloropyrimidine-5-carbonyl chloride (500 mg, 2.38 mmol) in dichloromethane (30 mL) was added methanol (87.6 mg, 2.73 mmol) and diisopropylethylamine (369 mg, 2.86 mmol) at 0 ¡ãC. The resulting mixture was stirred for at 0 ¡ãC 1 h. Then the solvent was removed. The residue (412mg, 2.0 mmol) was dissolved in IPA (20 mL) followed by the addition of Z-Ormthine (465 mg, 2.0 mmol) and N,N- diisopropylethylamine (388 mg, 3.0 mmol). The resulting mixture was stirred at 0 ¡ãC for 90 min, then dichloromethane (5.0 mL) was added. The resulting mixture was stirred at 0 ¡ãC for 1.0 h and at room temperature overnight. Solvent was removed and the residue (MS m/z 403.30 [M+H]+) was dissolved in DMF (5.0 mL) and was added dropwise into a solution of 1,4-diaminobutane (1.68g, 19.1 mmol) in DMF (1.0 mL) at room temperature. The resulting mixture was heated to 45 ¡ãC for l . The solvent was removed and the residue was dissolved in ethyl acetate (35 mL) and washed with water (3x). The organic layer was dried ( a2S04), filtered and concentrated. The residue was purified on HPLC to provide (S)-5-((2-((4- aminobutyl)amino)-5-(methoxycarbonyl)pyrimidin-4-yl)amino)-2-((tert-butoxycarbonyl) amino)pentanoic acid as a semisolid (MS m/z 455.30 [M+H]+). The semisolid (595 mg, 1.31 mmol) was dissolved in DMF (150 mL), then TBTU (546.4 mg, 1.70 mmol) and DIEA (508 mg, 3.93 mmol) were added sequentially. The resulting mixture was stirred at room temperature overnight. The solvent was removed. The residue was dissolved in ethyl acetate and washed with water (3x). The organic layer was dried (Na2S04), filtered and concentrated. The residue was purified on HPLC to provide the totle compound (UNC2343A). 1H NM (400 MHz, CD3OD) S 8.42 (s, 1H), 4.08-3.99 (m, 1H), 3.90-3.84 (m, 3H), 3.59-3.47 (m, 2H), 3.46-3.31 (m, 2H), 3.28-3.21 (m, 1H), 3.09-2.95 (m, 1H), 1.90-1.52 (m, 8H), 1.51- 1.32 (m, 9H); MS m/z 437.30 [M+H]+.

The synthetic route of 3177-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; ZHANG, Weihe; FRYE, Stephen; WO2015/157127; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 25940-35-6, Pyrazolo[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, Safety of Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, blongs to pyrimidines compound. Safety of Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

To the mixture of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (42 mg, 0.26 mmol) and diisopropylethylamine (0.09 mL, 0.52 mmol) in DMF (2 mL) was added 2-(7-aza-1H- benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (131 mg, 0.34 mmol) then the mixture was stirred at 25 oC for 15 min. To the mixture was added a solution of 2-[4-(5- amino-2,2-dimethyl-3H-benzofuran-6-yl)piperazin-1-yl]ethanol (50 mg, 0.17 mmol) in DMF (2 mL) and the resulting mixture was stirred at 25 oC for 16h. The mixture was purified by preparative HPLC(Xbridge 21.2*250 mm c18, 10um, A: acetonitrile 10-70%; B:10 mM ammonium bicarbonate in water) to afford N-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2,2- dimethyl-3H-benzofuran-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (45 mg, 60%) as a yellow solid.1H NMR (400 MHz,DMSO-d6) delta 10.42(s, 1H), 9.37(dd, J = 1.6 , 7.2Hz, 1H), 8.92 (dd, J = 1.6, 4.4Hz, 1H), 8.68(s, 1H), 8.31(s, 1H), 7.36(dd, J = 4.4,7.2Hz, 1H), 6.69(s, 1H), 4.45(t, J =5.2Hz, 1H), 3.54(q, J = 5.6 Hz, 2H), 3.00(s, 2H), 2.84-2.78(m, 4H), 2.74-2.61 (m, 4H), 2.50(t, J = 5.6 Hz ,2H), 1.41(s, 6H). MS (ESI): m/z = 437.3 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, and friends who are interested can also refer to it.

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

Synthetic Route of 153435-63-3, 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 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 3-8 (Trans)-8-[(2,5′-bipyrimidin-2′-Vlamino)methyl]-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decan-2-one To a solution of (trans)-8-{[(5-bromo-2-pyrimidinyl)amino]methyl}-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decan-2-one (Intermediate 24, 30 mg, 0.072 mmol) in dimethylsulfoxide (3 ml) 2-(tributylstannanyl)pyrimidine (26.5 mg, 0.072 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.32 mg, 2.87 mumol) were added and the resulting mixture was irradiated in a microwave oven at 120 C. for 10 min. The crude solution was first eluted on a SCX cartridge (DCM/MeOH/NH3 (2M soln in MeOH) 100/0/0 to 80/10/10) and evaporated to dryness. Purification by silica gel chromatography (SP1 automated instrument, SNAP 10 g Si cartridge, elution in gradient with 0%-10% MeOHDCM) gave the title compound as a white solid (15 mg, 0.036 mmol, 50%).

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Biagetti, Matteo; Contini, Stefania Anna; Genski, Thorsten; Guery, Sebastien; Leslie, Colin Philip; Mazzali, Angelica; Pizzi, Domenica Antonia; Sabbatini, Fabio Maria; Seri, Catia; US2009/203705; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia