Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 33034-67-2, 2-Chloro-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-Chloro-4-(trifluoromethyl)pyrimidine, blongs to pyrimidines compound. name: 2-Chloro-4-(trifluoromethyl)pyrimidine

tert-Butyl 2-cyano-2-[4-trifluoromethylpyrimidin-2 (1H)-ylidene]acetate. tert-Butyl 2-cyanoacetate (97.45 g, 690 mmol) was dissolved in anhydrous THF (1 L), and cooled on an ice-bath for 90 min with stirring under nitrogen. A 1M solution of lithium hexamethyldisilazane in THF (690 mL, 690 mmol) was added dropwise. The mixture was stirred for an additional 1 hr, then 2-chloro-4-trifluoromethylpyrimidin (105 g, 590 mmol) was added dropwise. The mixture was then heated to 50° C. for 3 hr with stirring under nitrogen, allowed to cool, and the solvent removed under reduced pressure. Hydrochloric acid (1N) was added to the residue to achieve a pH of 1-2. The precipitated solids were collected by filtration and dried under vacuum to give tert-butyl 2-cyano-2-[4-trifluoromethylpyrimidin-2(1H)-ylidene]acetate (135 g, 82percent yield) as a bright yellow solid, >98percent pure by LC/MS. tert-Butyl 2-cyano-2-[4-trifluoromethylpyrimidin-2(1H)-ylidene]acetate (48 g; 166 mmol) was suspended in 4M hydrogen chloride in dioxane (415 mL, 1.66 mol) and the mixture stirred at room temperature for 6 hr, then concentrated under reduced pressure to give 2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (31 g, 100percent yield) as an orange oil, >98percent pure by LC/MS. To a stirred solution of 2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (31.0 g; 166 mmol) in absolute ethanol (800 mL) was added potassium O-ethylxanthate (26.6 g; 166 mmol) followed by potassium carbonate (45.8 g; 332 mmol). The mixture was heated to 100° C. for 3 hr, cooled to room temperature, iodomethane (47.1 g; 332 mmol) added dropwise, and 1N hydrochloric acid (2 L) added. The resulting mixture was extracted with DCM (1.5 L), and the DCM layer was washed twice with brine (1 L each). The solvent was removed under reduced pressure to give 3,3-bis(methylthio)-2-(4-trifluoromethylpyrimidin-2-yl)acrylonitrile (36 g, 75percent yield) as a light brown solid, >95percent pure by LC/MS.

The synthetic route of 33034-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Telik, Inc.; US2010/81653; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6299-25-8 , The common heterocyclic compound, 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine, molecular formula is C5H4Cl2N2S, 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.

To a stirred solution of 4,6-dichloro-2- (methylthio)pyrimidine (50 g, 0.26 mol) in dichloromethane (1 L) at 00C was added meta-chloroperoxybenzoic acid (143.6 g, 0.64 mol) over a period of 20 minutes. The solution was allowed to warm to room temperature and was stirred for 4 hours. The mixture was diluted with dichloromethane (1.5 L) and then treated sequentially with 50% Na2S2O3 / NaHCO3 solution (2 x 200 ml), sat. NaHCO3 solution (4 x 300 ml), and brine (200 ml) then dried (MgSO4). The solvent was removed in vacuo to afford an off-white solid, which was redissolved in EtOAc (IL) and treated sequentially with sat. NaHCO3 solution (3 x 300 ml), and brine (100 ml) then dried (MgSO4). The solvent was removed EPO in vacuo to afford the title compound (A) as a white solid (55.6 g, 96% yield). 1H NMR CDCl3 delta 3.40 (3H5 s, CH3), 7.75 (IH. s. ArH).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/14250; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1208901-69-2, Adding some certain compound to certain chemical reactions, such as: 1208901-69-2, name is 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride,molecular formula is C7H8Cl3N3, 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 1208901-69-2.

Compound (D) (11.8 g, 49.1 mmol) prepared in Step 3 was dissolved in dichloromethane (300 mL), then cyclopropanecarbonyl chloride (5.4 mL, 1.2 equivalents) and triethylamine (20.4 mL, 3.0 equivalents) were added thereto and the mixture was stirred at room temperature for 1 hour. The resulting reaction solution was washed with water and a saturated sodium bicarbonate solution and dried over magnesium sulfate. After evaporating the solvent, diisopropyl ether was added to the residue and the suspension was stirred for not shorter than 1 hour. After that, the crystals separated out therefrom were filtered and dried in vacuo to prepare compound (E) (12.5 g, yield: 94%).

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. 1208901-69-2, 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1537879; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-61-4, 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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

To a solution of 2-chloro-5-methyl-pyrimidine (500.00 mg, 3.89 mmol, 1.00 eq) in MeOH (10.00 mL) and DMF (2.00mL) was added triethylamine (1.18 g, 11.67 mmol, 1.62 mL, 3.00 eq) and Pd(dppf)C12 (426.87 mg, 583.39 umol, 0.15 eq) under CO. The suspension was degassed and purged with CO several times. The mixture was stirred under CO (3 Mpa) at 120C for 16 h. The reaction mixture was filtered and the filtrate was concentrated. The crude residue was purified by column chromatography (Petroleum ether : Ethyl acetate=20: l to 0: 1) to afford methyl 5-methylpyrimidine-2-carboxylate (350.00 mg). LCMS (M+H+) m/z: 153.

Statistics shows that 22536-61-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methylpyrimidine.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COTE, Alexandre; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-christophe; VASWANI, Rishi, G.; (274 pag.)WO2016/172496; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]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, 90914-41-3, blongs to pyrimidines compound. Computed Properties of C5H2BrClN4

The resulting de- boc’ed residue was dissolved in TEtaF (5mL), and Et3N (0.1 mL) before adding 3-Bromo-4- Chloro-lH-pyrazolo[3,4-Patent; EXELIXIS, INC.; WO2006/71819; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10070-92-5, 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde, molecular formula is C5H4N2O, 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 stirred solution of N-cyclopropyl-5-methoxy-2-methylaniline Int-11 (200 mg, 1.12 mmol) in DMF (4 mL) and water (0.4 mL) under an inert atmosphere was added pyrimidine-5-carbaldehyde (182 mg, 1.68 mmol) and oxone (690 mg, 2.24 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 h. After consumption of starting material (by TLC), the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2*20 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluent: 2% MeOH/CH2Cl2) to afford 1-cyclopropyl-6-methoxy-2-(pyrimidin-5-yl)-1H-benzo[d]imidazole Ex. 25 (95 mg, 0.35 mmol, 32%) as an off white solid. ?H NMR (400 MHz, CD3OD): oe 9.36 (s, 2H), 9.28(s, 1H), 7.60 (d, J=8.8 Hz, 1H), 7.20 (d, J=2.3 Hz, 1H), 6.98(dd, J=8.8, 2.4 Hz, 1H), 3.92 (s, 3H), 3.78-3.76 (m, 1H),1.25-1.22 (m, 2H), 0.84-0.72 (m, 2H) EC-MS: mlz 267 [M+H] at 1.70 RT (98.22% purity). HPEC: 99.94%.

According to the analysis of related databases, 10070-92-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; (93 pag.)US2018/186773; (2018); A1;,
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. 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, the common compound, a new synthetic route is introduced below. Formula: C15H14N4O3

General procedure: To a suspension of compound 6 (0.033 mmol) in N,N-dimethylformamide (5 mL), corresponding amine (RNH2) (0.033 mmol) and DIPEA (0.1 mmol) were added at about 10 C under nitrogen atmosphere. To this, diethylphosphorocyanidate(0.04 mmol) was added slowly over a period of 15 min. The resultant solution was stirred for 3 h at about 10 C. The reaction was complete by TLC (TLC system: 10% methanol in chloroform). Reaction was slowly quenched using saturated sodium-bi-carbonate solution and the resulted solid was stirred for 30min. Solid was collected by filtration and the wet cake was washed with saturated sodium-bi-carbonate solution. Upon drying the wet cake for an hour under vacuum, it was further suspended in methanol and stirred for 30 min, filtered, collected and dried to get respective pure compounds.

The synthetic route of 137281-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Balaraman, Selvakumar; Nayak, Nagaraj; Subbiah, Madhuri; Elango, Kuppanagounder P.; Medicinal Chemistry Research; vol. 27; 11-12; (2018); p. 2538 – 2546;,
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.1208170-17-5, name is 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C7H6ClN3S, molecular weight is 199.66, as common compound, the synthetic route is as follows.category: pyrimidines

To a round bottomed flask was added (5)-1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine 2,2,2-trifluoroacetate (364 mg, 0.986 mmol) in THF (6400 mu) along with 4-chloro-6-methyl-2-(methylthio)pyrimidine-5 -carbonitrile (197 mg, 0.986 mmol) and Et3N (302 muEpsilon, 2.168 mmol). The reaction mixture was stirred at room temperature overnight and was subsequently purified on silica, eluting with a gradient of EtOAc/hexanes (2:8 to 9: 1) to give the title compound as a clear film (270 mg, 65.5%). ESI- MS m/z [M+H]+ calc’d for C21H22N8S 419.17; found 419.4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1208170-17-5, 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHANG, Edcon; NOTZ, Wolfgang Reinhard Ludwig; WALLACE, Michael B.; WO2014/11568; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3177-20-6, 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.3177-20-6, name is Methyl 2,4-dichloropyrimidine-5-carboxylate, molecular formula is C6H4Cl2N2O2, molecular weight is 207.0142, as common compound, the synthetic route is as follows.

A solution of methyl 2,4-dichloropyrimidine-5-carboxylate (27 mg, 0.13 mmol) in dichloroethane / i-butanol (1: 1, 2mL) was cooled to 0°C. ZnCl2 solution (1.0 M in ether, 0.29 mL, 0.29 mmol, 2.2 eq.) was added. After stirring for lh, a solution of (R)-methyl 1- isopropyl-7-(methylsulfonyl)-l,2,3,4-tetrahydrobenzo[4,5]imidazo[l,2-a]pyrazine-8- carboxylate (30 mg, 0.09 mmol) in dichloroethane / i-butanol (1: 1, 2 mL) was added slowly at 0°C. The mixture was stirred at rt overnight. Water (10 mL) was added and the mixture was extracted with EtOAc (10 mL X 3). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford (R)-methyl 2-(4-chloro-5-(methoxycarbonyl)pyrimidin-2-yl)-l- isopropyl-7-(methylsulfonyl)-l,2,3,4-tetrahydrobenzo[4,5]irnidazo[l,2-a]pyrazine-8- carboxylate (34 mg, 77.3percent yield) as a solid.

Statistics shows that 3177-20-6 is playing an increasingly important role. we look forward to future research findings about Methyl 2,4-dichloropyrimidine-5-carboxylate.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; DONG, Chengguo; FAN, Yi; LEFTHERIS, Katerina; LOTESTA, Stephen; SINGH, Suresh, B.; TICE, Colin; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2013/138568; (2013); A1;,
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. 83410-18-8, name is 5-Iodo-6-methylpyrimidin-4-amine, molecular formula is C5H6IN3, 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. Recommanded Product: 5-Iodo-6-methylpyrimidin-4-amine

Reference Example 14-Amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine4-Amino-5-iodo-6-methylpyrimidine and cuprous 4-(trifluoromethyl)phenylacetylide were reacted in pyridine while stirring under heating to obtain a target substance. The target substance was subjected to e.g., proton nuclear magnetic resonance spectrometry (1H-NMR) and mass spectrometry (MS) and confirmed as the titled compound. Furthermore, MS measurement result is shown.Mass spectrum: 278.

With the rapid development of chemical substances, we look forward to future research findings about 83410-18-8.

Reference:
Patent; Nishio, Tetsuya; US2011/319618; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia