Tag: M.W=300-400

Application of 147118-37-4, Adding some certain compound to certain chemical reactions, such as: 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide,molecular formula is C16H18FN3O3S, 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 147118-37-4.

Step D: Titanium tetrachloride (1M in dichloromethane, 12.67 mL) was added dropwise to a solution of 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)-5-pyrimidinecarbardehyde (2.13 g) (compound of formula (III-a)) in dry THF (60 mL) at 0C. After stirring for 15 minutes, a solution of compound of formula (II, PG=TBDMS, Z=OMe) (2 g) in dry THF (20 mL) and subsequently a solution of N-methylmorpholine (2.64 mL) in dry THF (20 mL) were slowly added. The reaction mixture was stirred at 0C for 3h, then quenched with water (40 mL) and extracted with EtOAc (3×40 mL). The combined organic layers were dried under vacuum and the resulting oil was purified via chromatographic column on silica gel (hexane/EtOAc 9:1) to give the 2.5 g of the corresponding racemic product of formula (I-a, PG=TBDMS, Z=OMe) (Molar yield = 68% yield). [0125] The 1 N-NMR spectrum is the same of that of the product of Example 4.

According to the analysis of related databases, 147118-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.I.S.- Fabbrica Italiana Sintetici S.p.A.; De Lucchi, Ottorino; Tartaggia, Stefano; Ferrari, Clark; Galvagni, Marco; EP2769979; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1421372-94-2, 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 1421372-94-2, name is N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

N-(4-fluoro-2-methoxy-5-nitro-phenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine (1300 mg, 3.3 mmol) dissolved in DMA (10 ml) and N-(4-fluoro-2-methoxy-5-nitro-phenyl)-4-(1- methylindol-3-yl)pyrimidin-2-amine (1.07 ml, 9.91 mmol) added followed by TEA (0.92 ml, 6.61 mmol) and the reaction heated to 140C for 30 minutes under microwave conditions and quenched with water (20 ml). The reaction mixture was extracted with ethyl acetate (3 x 20 ml). The combined organics were washed with water, dried over MgSO4 and concentrated in vacuo to a red solid. Used in subsequent steps with no further purification.

According to the analysis of related databases, 1421372-94-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARVINAS, INC.; YALE UNIVERSITY; GREW, Andrew, P.; ZIMMERMANN, Kurt; WANG, Jing; BERLIN, Michael; DONG, Hanqing; ISHCHENKO, Alexey; QIAN, Yimin; CREWS, Craig, M.; JAIME-FIGUEROA, Saul; BURSLEM, George; (855 pag.)WO2018/119441; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 330786-24-8, 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 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

The 3- (4-phenoxyphenyl) -1H-pyrazolo [3,4-d]pyrimidin-4-amine(compound 2a)(2.12g,7mmol), 3-hydroxypiperidine-1- tert-Butyl formate(1.55g,7.7mmol), Triphenylphosphine(2.75g,10.5mmol)and Azobisisobutyronitrile (2.12g,10.5mmol) dissolved in THF (250ml), keep thereaction at room temperature for 12h(TLC thin layer chromatography monitoringreaction is complete or not). After the completion of the reaction , solventwas recovered under reduced pressure. into the remaining reaction mixture added100 ethyl acetate, organic layer was extracted three times with Saturatedsodium carbonate solution 100ml*3, organic phases were combined, washed oncewith saturated sodium chloride and dried over anhydrous sodium sulfate. The solvent was recovered under reducedpressure to give 1.12 g of a brown solid in 33% yield.

According to the analysis of related databases, 330786-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANGZHOU HERTZ PHARMACEUTICAL CO LTD; ZHOU, XINGLU; HAN, LING; GE, ZHEN; LIU, XINGGUO; LUO, WENHUA; LIU, WENHUA; (27 pag.)CN104844609; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 862730-04-9, 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.862730-04-9, name is 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C8H10IN5, molecular weight is 303.1, as common compound, the synthetic route is as follows.

General Suzuki coupling. Preparation of final products (see Table 1 for final product names and structures); 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (40 mg, 0.13 mmol, 1 equivalent) was dissolved in DME (12 ml). Boronic acid (1.1 equivalent) was dissolved in EtOH (3.3 ml) and added to reaction mixture. Pd(PPh3)4 (30 mg, 0.026 mmol, 0.2 equivalents) and saturated Na2CO3 (1.9 ml) were added to the reaction mixture and heated to 80 C. under argon and refluxed for 8 hours. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined and solvent was removed. Resulting solid (or oil) was dissolved in dH2O-MeCN-trifluroacetic acid, 50:50:0.1 and purified by HPLC. Purified product (varying yields) was confirmed by LCMS.; Synthesis of 4-(4-Amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-benzenesulfonamide (BA14); A solution of benzenesulfonamide-4-boronic acid pinacol ester (23 mg, 0.08 mmol) in EtOH (3.3 mL) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (20 mg, 0.07 mmol) in DME (12 mL). Pd(PPh3)4 (16 mg, 0.014 mmol) and saturated Na2CO3 (1.9 mL) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA14 (2.2 mg, 10% yield). ESI-MS (M+H)+ m/z calcd 333.1, found 333.1.

Statistics shows that 862730-04-9 is playing an increasingly important role. we look forward to future research findings about 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 58536-46-2, Adding some certain compound to certain chemical reactions, such as: 58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine,molecular formula is C22H15BrN2, 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 58536-46-2.

General procedure: A mixture of 4-(4-bromophenyl)-2,6-diphenylpyrimidine (4.06 g, 10.5 mmol), compoundBFCz (2.57 g, 10 mmol), CuI (0.19 g, 1 mmol), K2CO3 (6.9 g, 50 mmol),18-crown-6 (0.264 g, 1 mmol) were dissolved in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU 10 mL) and stirred at 180 Cunder a nitrogen atmosphere for 48 h. After cooling to room temperature,the mixture was extracted with CH2Cl2 and water. The organicphase was dried over anhydrous MgSO4 and filtered. After removal ofthe solvent, the residue was purified by column silica gel chromatography(PE: DCM=10:1) and recrystallized to afford a white productin 64% yield (3.6 g).

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. 58536-46-2, 4-(4-Bromophenyl)-2,6-diphenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Qing; Xiang, Songpo; Huang, Zhi; Sun, Shuaiqiang; Ye, Shaofeng; Lv, Xialei; Liu, Wei; Guo, Runda; Wang, Lei; Dyes and Pigments; vol. 155; (2018); p. 51 – 58;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 862730-04-9, 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. 862730-04-9, name is 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C8H10IN5, 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.

Compound 2-4 is synthesized as shown in Scheme 2. Compound 1-3 is reacted with isopropyl bromide in dimethylformamide with potassium carbonate at 800C, to provide the 1 -isopropyl pyrazolopyrimidine 2-1. This intermediate with the protected indolyl boronic acid species 2-2, using tetrakistriphenylphosphine palladium catalysis in DME-water solvent at 800C for 4-5 hours, to produce the Suzuki coupling product, compound 2-3. Removal of the protecting groups with acid in dioxane yields the product, 2-( 4-amino-lH-pyrazolo[3,4-d]pyrimidin-3-yl iodide (Cpd. 2-4).

According to the analysis of related databases, 862730-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTELLIKINE, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; MARTIN, Michael; ROMMEL, Christian; WO2010/6086; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1197953-49-3, 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 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. This compound has unique chemical properties. The synthetic route is as follows.

2-[D3]methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline (1.25 g, 4.06 mmol), (2-((2,5-dichloropyrimidin-4-yl)amino)phenyl)dimethyl phosphine oxide (the compound of Formula IV) (0.92 g, 2.90 mmol), 14% hydrogenchloride-ethanol (7.5 g, 29 mmol) and ethylene glycol monomethyl ether (22mL) were respectively added in a 35 mLpressure tubing, heated in a microwave to 120C and reacted for 5.5 hours. After the reaction was completed, thereaction solution was cooled down to room temperature and evaporated under reduced pressure to remove the solvent.The residue was dissolved in dichloromethane (60mL) and adjusted to alkaline pH by adding saturated sodium carbonatesolution. The resulting solution was separated. The organic phase was washed with saturated brine (30 mL), dried overanhydrous sodium sulfate, and evaporated under reduced pressure to remove the solvent. The residue obtained wassubjected to silica gel column chromatography (mobile phase, dichloromethane : methanol : triethylamine = 300 : 30 :1.5) to give a crude product. The crude product was beaten with ethyl acetate (10 mL) to give (2-((5-chloro-2-((2-[D3]methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)dimethyl phosphorusoxide (0.18 g, 11.0% yield), with >98% of D3 content.1H-NMR(300 MHz, CDCl3): delta = 10.80 (s, 1H), 8.62 (dd, J = 4.4, 8.2 Hz, 1H), 8.09-8.08 (m, 2H), 7.47 (dd, J = 7.7, 8.0Hz, 1H), 7.31-7.25 (m, 1H), 7.11 (dd, J = 7.4, 7.0 Hz, 1H), 6.54 (s, 1H), 6.48 (dd, J = 1.4, 8.4 Hz, 1H), 3.65 (d, J = 12.2Hz, 2H), 2.73-2.41 (m, 11H), 2.37 (s, 3H), 1.95 (d, J = 11.2 Hz, 2H), 1.85, 1.80 (2s, 6H), 1.73-1.66 (m, 2H).13C-NMR (75 MHz, CDCl3) : delta = 157.76, 155.87, 154.93, 149.29, 147.48, 143.90, 143.87, 132.33, 132.30, 129.52,129.37, 123.10, 123.01, 122.44, 122.27, 122.09, 120.58, 119.55, 108.36, 105.99, 101.01, 61.78, 55.27, 50.46, 48.78,45.83, 28.19, 19.02, 18.08.HRMS (ESI, [M+H]+) m/z: 587.2861.

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 1197953-49-3, (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; ZHANG, Yinsheng; LIU, Baomin; YANG, Beibei; (35 pag.)EP3381925; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 252723-17-4, 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 252723-17-4, name is 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 7-Benzenesulfonyl-5-bromo-4-chloro-7H-pyrrolo [2,3- d] pyrimidine (4.9 g, 13 mmol), Piperazine-l-carboxylic acid tert-butyl ester (3.7g, 20 mmol), and DIPEA (5.7 mL, 33 mmol) in IPA (30 mL) was stirred and heated at reflux for 6 hours. The mixture was cooled to-10 C, the solids collected by vacuum filtration, rinsed with cold IPA and dried under vacuum to give 4- (7-Benzenesulfonyl-5-bromo-7H-pyrrolo [2,3- d] pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (5.9g, 86%. ) LCMS (APCI+) m/z 522 and 524 [M+H] + ; Rt: 3.92 min. 1H NMR (DMSO-d6,400 MHz) 5 8. 48 (1H, s), 8.21 (2H, d, J 8. 2 Hz), 7.66-7. 62 (2H, m), 7.54 (2H, t, J 7. 8 Hz), 3.62-3. 55 (8H, m), 1. 48 (9H, s.)

According to the analysis of related databases, 252723-17-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2005/51304; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 147118-37-4, 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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide. A new synthetic method of this compound is introduced below.

(1) Synthesis of 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-acrylonitrile Add 30 g of 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-formaldehyde into a reaction flask of 500 ml, add toluene 130 ml, and start to agitate. Add in turn phosphate diethylacetonitrile 20.5 g and Aliquat336 (catalyst) 1.4 g, and titrate with 20% sodium hydroxide solution 62.7 g below 25 C., with the reaction solution gradually clarifying and turning out to be a pink clear solution after titration. React for 3 hours at room temperature, and a white solid precipitates. Filter with a pump, wash with water, pump, and dry, and obtain a white solid 30.5 g with a yield of 95.4%. Add 30 g of 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-formaldehyde into a reaction flask of 500 ml, add toluene 140 ml, and start to agitate. Add in turn phosphate diethylacetonitrile 16.4 g and Aliquat336 1.6 g, and titrate with 20% sodium hydroxide solution 60.5 g below 25 C., with the reaction solution gradually clarifing and turning out to be a pink clear solution. React for 4 hours at room temperature, and a white solid precipitates. Filter with a pump, wash with water, drain with a pump, dry, and obtain a white solid 28.5 g, with a yield of 89.1%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147118-37-4, N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Anhui Quingyun Pharmaceutical and Chemical Co., Ltd.; US2008/91014; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 764659-72-5, 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.764659-72-5, name is (2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate, molecular formula is C18H26FN3O4S, molecular weight is 399.4802, as common compound, the synthetic route is as follows.

EXAMPLE-13: Synthesis of 4-amino-5-fluoro-1-(2 ?-hydroxymethyl-[1,3]-oxothiolane- 5S-yl)1tf-pyrimidin-3-one. 2-fluorobenzoic acid salt (formula-8b1); Dipotassium hydrogen orthophosphate (83.3 g) was dissolved in a mixture of industrially methylated spirit (IMS, 600 mL) & purified water (200 mL) and the obtained solution was cooled to 18C. The compound of formula-7b (100 g, 0.26 mol) was added at 15-22C and the suspension was stirred at 18-22C for 1 h. A solution of sodium borohydride (20. 4 g (0.54 mol) in water (110 mL) containing sodium hydroxide (40 mg)) was added drop wise by keeping temperature at 18-22C and maintained for 4 h. The completion of the reaction was confirmed by TLC. The reaction mass was transferred into a separating funnel and the layers were separated. The organic layer pH was adjusted to 5.9-6.3 with aq. HCI (~25 mL) and readjusted to pH 7.5-7.8 with sodium hydroxide (15 mL, 15% w/w) and filtered. IMS (~790 mL) was distilled out initially atmospherically followed by reduced pressure to reduce the traces of IMS. The resultant residue was diluted with water (200 mL) and then cooled to 22-30C. Toluene (150 mL) was added to the reaction mass under stirring, allowed the layers to settle and separate the layers. Toluene layer was washed with water (100 mL) and combined aqueous layer was charcoalized. The filtrate was warmed to 38-42C, 2- fluorobenzoic acid (37 g, 0.26 mol) was added and stirred for 2h at the same temperature. The reaction mass was cooled to 22-30C and maintained for 3-4h. The separated solid was filtered and washed with pre-cooled water and dried to get compound of formula-8b. in 80 g. 1H NMR (300 MHz, DMSO-d6): delta 13.40 (brs, 1H), 8.20 (d, 1 H, J=7.2 Hz), 7.84-8.00 (m, 2H), 7.58-7.68 (m, 2H), 7.28-7.34 (m, 2H), 6.12-6.16 (m, 1H), 5.41 (t, 1 H, J=5.4 Hz), 5.18-5.20 (t, 1 H, J=3.9 Hz), 3.70 -3.82 (m, 2H), 3.39-3.45 (m, 1H), 3.09-3.15 (dd, 1 H, J=11.85 & 4.35 Hz).

Statistics shows that 764659-72-5 is playing an increasingly important role. we look forward to future research findings about (2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate.

Reference:
Patent; MATRIX LABORATORIES LTD.; RAMA, Shankar; GORANTLA, Sarat, Chandra, Srikanth; VADALI, Lakshmana, Rao; INUPAKUTIKA, Venkata, Bala, Kishore, Sarma; DASARI, Srinivas, Rao; MITTAPELLY, Nagaraju; SINGH, Santosh, Kumar; DATTA, Debashish; WO2011/95987; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia