Tag: M.W:200-300

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. 1152475-50-7, name is 2-Chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below., Formula: C6H3ClIN3

To a stirred solution of 2-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine (110 mg, 0.39 mmol) in DCM (5 ml) was added tetrabutylammonium bromide (19 mg, 0.06 mmol), NaOH (1 ml, 2M) and MeI (47 mul, 0.47 mmol) were added and the mixture was stirred for 16 hours at room temperature. Water, DCM and EtOAc were added and the phases were separated. Concentration by evaporation followed by trituration using Et2O gave 110 mg (94%) of the title compound. LC/MS (20-100% CH3CN:0.05% HCOOH(aq) gradient over 5 min): 3.07 min. 294 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, 1152475-50-7, 2-Chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; PFIZER INC.; Schnute, Mark Edward; Wennerstal, Goeran Mattias; Blinn, James Robert; Kaila, Neelu; Kiefer, JR., James Richard; Mente, Scot Richard; Kurumbail, Ravi G.; Meyers, Marvin Jay; Thorarensen, Atli; Xing, Li; Zapf, Christoph Wolfgang; Zamaratski, Edouard; Flick, Andrew Christopher; Jones, Peter; (77 pag.)US2016/46597; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 7627-39-6, 2,4-Dichloro-5-(ethoxymethyl)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, Recommanded Product: 2,4-Dichloro-5-(ethoxymethyl)pyrimidine, blongs to pyrimidines compound. Recommanded Product: 2,4-Dichloro-5-(ethoxymethyl)pyrimidine

A yellow slurry mixture of (S)-3 -hydroxy- 10-methyl-9, 10, 11,12-tetrahydro-8H- [l,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one (30 g, 100 mmol), 2,4-dichloro-5- (ethoxymethyl)pyrimidine (24.90 g, 120 mmol), and potassium carbonate (325 mesh) (16.96 g, 120 mmol) in DMSO (150 ml, 2114 mmol) and THF (150 ml, 1831 mmol) was stirred at ambient temperature for 5 – 10 minutes, followed by heating at 40 – 45 C for at least 16 hours with sufficient agitation (350 – 400 rpm). The yellow/tan slurry mixture was then cooled to 20 – 25 C, and filtered over 9 g of Celite (prewetted with 15 mL of THF). The yellow filtrate (-400 ml) was transferred back to the visually clean jacketed flask along with 240 mL of THF, and was heated to 40-45 C over 30 minutes. To the mixture was charged 150 mL of 10 wt% aqueous NaCl, stirred for 5 minutes and settled for phase split. After the bottom aqueous phase was removed, 150 mL of THF and 150 mL of 10 wt% aqueous NaCl were charged and stirred at 40- 45 C for 5 minutes. The aqueous phase was removed again. Then, 90 mL of THF and 50 mL of 10 wt% aqueous NaCl were charged,maintining the batch temp at 40-45 C (lower temp will make product crystallize out). The aqueous phase was removed and the remaining organic portion was distilled under atmospheric pressure at 65-70 C to ~ 300 ml. The batch was seeded with 200 mg of the product and the resulting mixture was aged for one hour. Then the batch was distilled with addition of isopropanol (600 ml) at a rate sufficient to maintain a constant batch volume. The slurry was cooled from -70 C to 22 C over 4 hours, hold at 22 C for 16 hours and filtered, washed with 3 x 30 mL of IP A, and dried in a vacuum oven at 40-45 C for 12-16 hours to afford a yellow solid (41.1 g, 87% yield); HPLC: Waters Ascentis Express C-18 HPLC column, 10 cm X 4.6 muiotaeta, 1 mL/min, 234 nm, gradient at 100% 0.1% H3P04to 100% CH3CN in 10 min, then hold at 100% CH3CN for 5 min): tR= 6.40 min (99.0%). 1H NMR (300 MHz, DMSO-i) delta ppm 1.13 – 1.27 (m, 6 H) 3.42 – 3.54 (m, 2 H) 3.57 – 3.70 (m, 3 H) 4.66 (s, 2 H) 7.18 (br t, J=5.18 Hz, 1 H) 7.64 (d, J=9.08 Hz, 1 H) 7.87 (d, J=8.89 Hz, 1 H) 8.12 – 8.23 (m, 2 H) 8.72 (s, 1 H) 9.37 (d, J=9.17 Hz, 1 H);13C NMR (75 MHz, DMSO- ) delta ppm 15.47, 19.12, 48.46, 52.39, 64.02, 66.28, 114.87, 115.10, 119.60, 124.30, 126.49, 126.75, 127.7, 135.77, 139.30, 145.00, 145.84, 156.32, 158.02, 160.48, 164.52, 167.37. LC/MS m/e+= 470. Anal. Calcd. for C22H2oN503SCl: C, 56.23; H, 4.29; N, 14.90; S, 6.82; CI, 7.54. Found: C, 55.87; H, 4.33; N, 14.61; S, 6.60.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7627-39-6, 2,4-Dichloro-5-(ethoxymethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CELGENE CAR LLC; MALONA, John; RUCHELMAN, Alexander L.; (117 pag.)WO2018/170204; (2018); 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.33097-13-1, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H3Cl2N3S, molecular weight is 220.08, as common compound, the synthetic route is as follows.Safety of 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile

Example 43 Synthesis of 5-(4-(2-cyano-3-cyclopropylacrylamido)benzylamino)-7-(3,5-dimethoxyphenylamino)-imidazo[1,2-c]pyrimidine-8-carboxamide Step 1. To a solution of 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (14 g, 63.6 mmol, 1.0 eq) and 3,5-dimethoxyaniline (9.94 g, 63.6 mmol, 1.0 eq) in THF (300 mL) at 0 C., was added DIEA (12.32 g, 95.4 mmol, 1.5 eq). The resulted mixture was stirred at RT for 4 h. The reaction mixture was diluted with water (30 mL), filtered and dried to give 4-chloro-6-(3,5-dimethoxy-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile (19 g, 89% in yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33097-13-1, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Taunton, JR., John William; Brameld, Kenneth Albert; Goldstein, David Michael; Mcfarland, Jesse; Krishnan, Shyam; Choy, Jonathan; US2014/323464; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 51940-64-8, 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.51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, molecular weight is 221.0407, as common compound, the synthetic route is as follows.

Potassium carbonate (62.50 g, 452.41 mmol) was added to ethyl 2,4-dichloropyrimidine-5-carboxylate (40.00 g, 180.97 mmol) and tetrahydro-2H-pyran-4-amine hydrochloride (24.90 g,10 181.0 mmol) in acetonitrile (1 L). The reaction mixture was stirred at rt for 16 h. The resultingprecipitate was collected by filtration, washed with THF (750 mL) and the combined organic layerswere concentrated in vacuo. The crude product was purified by fcc, elution gradient 0 to 2% THFin DCM, to afford the title compound (37.74 g, 73%) as a pale yellow solid; 1H NMR (400 MHz,DMSO) 1.32 (3H, t), 1.54-1.63 (2H, m), 1.85-1.89 (2H, m), 3.43-3.49 (2H, m), 3.83-3.88 (2H, m),15 4.12-4.26 (lH, m), 4.29-4.34 (2H, m), 8.34 (lH, d), 8.64 (lH, s); m/z MH+ 286.

The chemical industry reduces the impact on the environment during synthesis 51940-64-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; HOWARD, Martin, Richard; TING, Attilla, Kuan, Tsuei; (145 pag.)WO2019/238929; (2019); 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. 38696-20-7, name is 5-Bromo-2-phenylpyrimidine, molecular formula is C10H7BrN2, 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-Bromo-2-phenylpyrimidine

Subsequently, 0.96 g of 5-bromo-2-phenylpyrimidine obtained in the above step 1, 1.21 g of 2,6-dimethylphenylboronic acid, 0.87 g of sodium carbonate, 0.76 g of bis (triphenylphosphine) palladium (II) dichloride (Abbreviation: Pd (PPh 3) 2 Cl 2), 15 mL of water and 15 mL of acetonitrile were placed in a recovery flask equipped with a reflux tube and argon bubbling was carried out for 15 minutes. The reaction vessel was heated by irradiating microwave (2.45 GHz 100 W) for 3 hours. Here, 1.21 g of 2,6-dimethylphenylboronic acid, 0.87 g of sodium carbonate and 0.035 g of Pd (PP 3) 2 Cl 2 were placed in a flask and argon bubbling was carried out for 15 minutes. This reaction vessel was heated again by irradiating microwave (2.45 GHz 100 W) for 3 hours. Thereafter, the obtained mixture was suction filtered with water. The obtained solid was purified by flash column chromatography using toluene as a developing solvent to obtain the desired pyrimidine derivative Hppm 2-dmp (white powder, yield 64percent).

With the rapid development of chemical substances, we look forward to future research findings about 38696-20-7.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY COMPANY LIMITED; INOUE, HIDEKO; HARA, TOMOKA; SEO, SATOSHI; SASAKI, TOSHIKI; SUZUKI, KUNIHIKO; (60 pag.)JP2016/6041; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26032-72-4 ,Some common heterocyclic compound, 26032-72-4, molecular formula is C10H6Cl2N2, 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.

2.3 g (10 mmol) of intermediate product (A), 7.5 g (22 mmol) of l-(4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)isoquinoline (D), and 0.6 g (0.5 mmol) of tetrakis-(triphenylphosphine)palladium were suspended in a mixed solvent of 70 ml of tetrahydrofuran and 50 ml of toluene to provide a suspension. The suspension was added to a solution in which 5.7 g (41 mmol) of potassium carbonate was dissolved in 50 ml of water. The obtained mixture was heated and refluxed for 12 hours. After separating the reaction fluid into two layers, an organic layer thereof was washed with a saturated sodium chloride aqueous solution and dried with anhydrous sodium sulfate. <134> The organic solvent was disti Hated and removed under reduced pressure, and then the residue was recrystallized with toluene. The extracted crystal was separated by filtration and washed with toluene to obtain 3.9 g (yield- 68.0 %) of compound (10).<135> 1H NMR (300MHz, CDCl3) 8.94 (d,2H), 8.68 (d,2H), 8.52 (d,2H), 8.39(d,2H), 8.21 (d,2H), 8.16 (s,lH), 7.94 (m,6H), 7.72 (m,4H), 7.61 (m,5H); MS[M+1] 563.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26032-72-4, its application will become more common.

Reference:
Patent; CHEIL INDUSTRIES INC.; KIM, Nam-Soo; KANG, Myeong-Soon; JUNG, Ho-Kuk; KANG, Eui-Su; PARK, Young-Sung; CHAE, Mi-Young; PARK, Jin-Seong; WO2010/24572; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 733039-20-8, Adding some certain compound to certain chemical reactions, such as: 733039-20-8, name is 5-Bromo-2-chloro-N-cyclopentylpyrimidin-4-amine,molecular formula is C9H11BrClN3, 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 733039-20-8.

Compound 2 (10.0 g, 36.2 mmol, 1.0 eq) was added at room temperature.N-methylpyrrolidone (NMP, 50 mL),Crotonic acid (4.7 g, 54.6 mmol, 1.5 eq) and triethylamine (14.7 g, 144.9 mol, 4.0 eq).The container is passed through three times of nitrogen,PdCl 2 (0.195 g, 1.10 mmol, 0.03 eq) was added to the exhausted reaction mixture.Three more nitrogen passes.After the raw materials are stirred and dissolved at room temperature,Rapidly warm up to 75 C,The stirring reaction was closed for 6 h,Sampling (diluted with ethyl acetate),TLC detection (DCM: MeOH = 12:1),The starting compound 1 is completely reacted,Add acetic anhydride to react 0.5h sampling point plate,The intermediate reaction is complete,The reaction mixture will be brought to 20 C,Add triethylamine hydrobromide solution (100 mL),Stir for 1h,Filtering,Water washing,Get a gray solid. Add ethyl acetate to dissolve,Add anhydrous magnesium sulfate to dry the mixture,Insoluble matter (salt and insoluble catalyst) is filtered out,Wash with ethyl acetate.Concentrate the filtrate to a low volume,Add n-hexane,Beating at 65 C for 30 min,Cool to 20 C and stir for 1 h.Filtering the solid,Vacuum drying,Obtained a brownish yellow solid,That is, Compound 1 (9.04 g, yield 94.8%, purity 99.1%).

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. 733039-20-8, 5-Bromo-2-chloro-N-cyclopentylpyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Ma Qingtong; Shan Xiaoyan; Chen Xudong; Chen Yu; (7 pag.)CN108117550; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13544-44-0, 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 13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To 2,4-dichloro-5-iodopyrimidine (4.00 g, 14.6 mmol), 2,4-difluorobenzylamine (2.26 mL, 19.0 mmol) and ethanol (44.2 mL) were added and the mixture was heated and stirred for 6 hours under reflux. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The residue was triturated with diisopropyl ether and a small amount of isopropyl alcohol, and then the solid was collected by filtration to obtain 2-chloro-4-(2,4-difluorobenzyl)-5-iodopyrimidine (Compound A1a) (3.44 g, 62%).

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 13544-44-0, 2,4-Dichloro-5-iodopyrimidine.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1595869; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 62458-96-2, 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one, 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, Computed Properties of C14H15N3O, blongs to pyrimidines compound. Computed Properties of C14H15N3O

B. 7-Benzyl-4-chloro-5, 6,7, 8-tetrahydropyrido [3, 4-d] pyrimidine [00228] 7-Benzyl-5, 6,7, 8-tetrahydro-3H-pyrido [3,4-d] pyrimidin-4-one (9.4g, 39mmol) was dissolved in anhydrous 1,2-dichloroethane and stirred under N2 (g) atmosphere. To the mixture was added POC13 (29mL, 312mmol), followed by N, N-dimethyl aniline (4.75g, 39mmol). The mixture was refluxed for 2 h and the solvents were removed under vacuum to give a red residue. The residue was dissolved in 20 mL of ethyl acetate and 20ml of water was added. The solution was neutralized with ice and solid NaHC03. After neutralization, ethyl acetate was added and the orgarhC layer’was washed with water ana Dnne. ine organic layer was dried over Na2SO4 and the solvents were removed under vacuum. The resulting red residue was purified using a gradient of ethyl acetate: hexane (0-100%) to give the desired compound as yellow crystals (3.8g, 38%).

The synthetic route of 62458-96-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WO2005/66171; (2005); 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, Recommanded Product: 90914-41-3, blongs to pyrimidines compound. Recommanded Product: 90914-41-3

Step 5: Synthesis of 4-(4-((1-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-yl)amino)-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (144): To a solution of 4-(6-methoxy-4-(piperidin-4-ylamino)naphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (143) (196 mg, 0.43 mmol) and triethylamine (0.5 ml) in anhydrous tetrahydrofuran (8 ml) was added 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (122 mg, 0.52 mmol). The mixture was stirred at 50 C. for 24 hours before being poured into ethyl acetate (150 ml) washed with water (300 ml) and the organic layer dried over anhydrous magnesium sulfate. Evaporation to dryness gave a yellow foam that was crystallized from dichloromethane and ethyl acetate to give 4-(4-((1-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-yl)amino)-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (144) as a yellow solid (145 mg) M.p.=167-172 C. 1H NMR (DMSO-d6) 400 MHz delta 8.4-8.33 (m, 2H), 7.9-7.8 (m, 2H), 7.52 (m, 2H), 7.24-7.2 (m, 1H), 7.15-7.12 (m, 1H), 5.9-5.74 (m, 1H), 4.56-4.53 (m, 2H), 3.95 (s, 1H), 3.9 (s, 3H), 3.41-3.26 (m, 2H), 3.22 (s, 6H), 2.28-2.25 (m, 2H), 1.97-1.75 (m, 2H), LCMS m/e 574 and 576 (M+) Calculated for C27H28BrN9O.CH2Cl2: C, 51.00; H, 4.59; N, 19.12; found C 51.00, H 4.39, N 18.85.

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; ArQule, Inc.; US2011/166137; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia