Tag: M.W=300-400

Electric Literature of 862730-04-9 ,Some common heterocyclic compound, 862730-04-9, molecular formula is C8H10IN5, 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.

Synthesis of 1-isopropyl-3-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA49); A solution of 3-Methoxyphenylboronic acid (17 mg, 0.11 mmol) in EtOH (3.3 ml) was added to a solution-of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (30 mg, 0.10 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 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 BA49. ESI-MS (M+H)+ m/z calcd 284.1, found 284.0.

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. 862730-04-9, 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

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

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. 139756-21-1, name is 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Example 1 Preparation of 5-(2-ethoxy-5-chlorosulfonyl)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyr azolo[4,3-d]pyrimidine-7-one Chlorosulfuric acid (50ml)was added into a 100ml three-neck flask with a stirrer, 5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidi ne-7-one (31.2g (0.1mol)) was added in batches under stirring in an ice bath. The reaction was exothermic and was performed for 12 hrs. The reaction solution was slowly poured into icy water (100g), a white solid was separated out, filtered, dried. A white solid (30g)was obtained with a yield of 76%.

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, 139756-21-1, 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one.

Reference:
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; WANG, Jianping; WANG, Jianguo; EP2666776; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 934524-10-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 934524-10-4 as follows.

To a solution of 3-propylthiophene (1.3 g, 10 mmol) in anhydroud THF (25 rnL) cooled at -78 0C under argon atmosphere was added ra-BuLi (2.5 M in hexanes; 4.4 mL, 11 mmol). The mixture was stirred at the same temperature for 15 min and trimethyllborate added (2.2 mL, 20 mmol). The resulting mixture was stirred at at -78 0C for 15 min and then stirred at RT for 2 h. The reaction was quenched with IM HCl (3 mL) and concentrated. The residue was taken up in water (40 mL) and extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the crude product purified by silica gel column (CHCl3 to 10% CH3OH/CHCI3) to afford 4-propylthiophen-2-yl-2-boronic acid as an off-white solid (0.5 g, 29%). A mixture of 8 (0.28 g, 0.82 mmol), 4-propylthiophen-2-yl-2-boronic acid (0.17 g, 1.0 mmol), Pd(PPh3)4 (96 mg, 0.08 mmol) and Na2CO3 (0.32 g, 3 mmol) in anhydrous DMF (10 mL) was degassed with argon for 2 min and then heated at 120 0C in a sealed tube for 2 h. After cooling to room temperature, the solvent was removed by rotovap. The crude product was then purified by silica gel column with 1 : 1 hexanes/CHCl3 as an eluent to yield a yellow solid (90 mg, 25%).[0346] 1H NMR (500 MHz, CDCl3): delta 0.96 (t, J = 7.4 Hz, 3H), 1.60-1.75 (m, 2H), 2.42 (s, 3H), 2.63 (t, J = 1.6 Hz, 2H), 6.95 (d, J = 4.0 Hz, IH), 7.22 (s, IH), 7.74 (d, J = 4.2 Hz, IH), 7.79 (s, IH), 8.13 (d, J = 8.4 Hz, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934524-10-4, its application will become more common.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, 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 C15H13ClN2O4, blongs to pyrimidines compound. Computed Properties of C15H13ClN2O4

Methyl (¡ê)-2-{2-[6-chloropyiimidin-4-yloxy]phenyl}-3-methoxyacrylate (E) (3g of 95.4% strength) was charged to the reaction tube followed by the solvent (10 ml) then 2- cyanophenol (1.2g), base (1.5 mol equivalents) and the compound being tested as a catalyst (15 mol%). The reaction mixtures were held, with stirring, at 400C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for formation of product, throughout the hold period, by Gas Chromatography. Results are recorded as area % levels of methyl (¡ê)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (II) and methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE l The results are shown in Table 2 below:TABLE 2; Further screening experiments, using DMF as a solvent, were carried out as detailed below: Methyl (¡ê)-2-{2-[6-chlororhoyrimidin-4-yloxy]ph.enyl}-3-methoxyacrylate (H) (6.4g of 45.2% strength solution in DMF) was charged to the reaction tube followed by further DMF (6.4 g), 2-cyanophenol (1.2g), potassium carbonate (1.5 mol equivalents) and the compound being tested as a catalyst (10 mol%). The reaction mixtures were held, with stirring, at 4O0C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for loss of starting material and formation of product, throughout the hold periods, by Gas Chromatography. Results are recorded as area % levels of methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (II) and methyl (2s)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE 3The results are shown in Table 4 below:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 147118-36-3, 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. 147118-36-3, name is 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsufonyl)amino]pyrimidine-5-yl-methanol, molecular formula is C16H20FN3O3S, 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 2 N-[5-(Diphenylphosphinoylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide 282.8 mg (0.80 mmol) of [4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulphonylamino)pyrimidin-5-yl]methanol was initially charged in 4.5 ml of xylene (isomer mixture) and admixed with 55 mg (1.30 mmol) of sodium hydride (55 percent dispersion in mineral oil). After 35 min, 185 mg (0.84 mmol) of chlorodiphenylphosphine in 1.5 ml of xylene was added at room temperature with vigorous stirring over a period of 5 min, and the mixture was subsequently heated at 135 C. for 20 h. After cooling to room temperature, the mixture was admixed with 15 ml of water and extracted with 10 ml of ethyl acetate. The organic phase was separated off and the aqueous phase was extracted with 2*10 ml of ethyl acetate. The combined organic phases were subsequently dried (MgSO4) and concentrated under reduced pressure. This gave 510 mg of crude product which was purified by silica gel chromatography (mobile phase: n-hexane/ethyl acetate 1:2, then ethyl acetate), and 230 mg (53.5 percent) of N-[5-(diphenylphosphinoylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulphonamide was isolated in the form of a colorless solid.

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 147118-36-3, 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsufonyl)amino]pyrimidine-5-yl-methanol.

Reference:
Patent; Lonza AG; US6160115; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 58536-46-2, 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.58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine, molecular formula is C22H15BrN2, molecular weight is 387.27, as common compound, the synthetic route is as follows.

General procedure: Intermediate 8 (2.9g, 10.0 mmol), Intermediate 2 (3.9g, 10.0 mmol), Pd(PPH3)4 (0.21g, 0.2 mmol), toluene (30 mL) and a 2M aqueous solution of potassium hydroxide (15 mL) were mixed under an argon atmosphere. The mixture was stirred at 80C for 7 hours. Water was added to the reaction solution to precipitate solid matters. The solid matters were washed with methanol. The solid matters obtained were filtrated and washed with heated toluene, and then dried to obtain 3.8 g of pale yellow powder. The pale yellow powder was identified as Aromatic amine derivative (H1) by FD-MS analysis.

Statistics shows that 58536-46-2 is playing an increasingly important role. we look forward to future research findings about 4-(4-Bromophenyl)-2,6-diphenylpyrimidine.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; KATO, Tomoki; ITO, Mitsunori; INOUE, Tetsuya; OGIWARA, Toshinari; HIBINO, Kumiko; EP2589596; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 153435-63-3, Adding some certain compound to certain chemical reactions, such as: 153435-63-3, name is 2-(Tributylstannyl)pyrimidine,molecular formula is C16H30N2Sn, 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 153435-63-3.

A solution of 2-tributylstannanyl pyrimidine (390 mg, 1.05 mmol) , 2-pyrimidin triflate intermediate (13) (510 mg, 0.81 mmol), and Pd(PPh3)4 (95 mg, 0.081 mmol) in dry dimethylacetamide (7.5 mL) was heated at 130C for 6 h. After being cooled to room temperature, the reaction was filtered through a plug of Celite, the filtrate was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, solvent was removed and the residue was purified by silica gel chromatography furnishing the desired compound as a pale yellow solid (357 mg, 79 %) . The crude bosentan was further purified by recrystallization in hot ?0 / EtOH affording pure bosentan monohydrate (1) as a white solid (327 mg, 70 %) .^-RMN (200 MHz, d6-DMSO) : 1.29 (s, 9H) ; 3.85 (m, 2H) ; 3.93 (s, 3H) ; 4.59 (m, 2H) ; 6.81-7.18 (m, 4H) , 7.43 (d, J = 8.0 Hz, 3H) ; 8.45 (d, J = 8.0 Hz, 2H) ; 9.01 (s, 2H) ppm.DSC-TG: endothermic peak at 116.53 C, with a loss of weight of 3.1 % (monohydrate) . Dio : 1.36 um, D50 : 20.32 muiotaeta, D90 : 56.64 muiotaeta

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; LABORATORIOS LESVI, S.L.; RODRIGUEZ ROPERO, Sergio; HUGUET CLOTET, Juan; WO2011/117143; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine. A new synthetic method of this compound is introduced below., Safety of 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine

Isopropanol (445 kg) was added to 2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine (70.2 kg, 203 mol, 1.15 eq.) and 2-Isopropoxy-5-methyl-4-(piperidin-4-yl)aniline dihydrochloride (56.7 kg, 176 mol). The mixture was heated for approx. 16 hours at reflux. Water (47 kg) was added and the mixture cooled to 0 C. The solid was filtered and washed with isopropanol/water. To the wet product, isopropanol (680 kg) and water (55 kg) was added and the slurry heated to reflux. The obtained clear solution was cooled to 0 C., filtered and dried under vacuum to yield 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine dihydrochloride (=ceritinib dihydrochloride; 84.5 kg [t.q., contains 10% w/w isopropanol], 76.0 kg [100%], 68% yield). Ethanol (155 kg) and water (113 kg) were added to 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-dihydrochloride; 45.0 kg [t.q., contains 10% w/w isopropanol], 40.5 kg [100%], 64.2 mol) and the mixture heated to 55 C. Aqueous NaOH (147 L of a 1 M solution, 2.3 eq.) was added slowly and then cooled to 20 C. After filtration, the product was recrystallized from ethanol and dried under vacuum to yield ceritinib (33.2 kg, 93% yield based on ceritinib dihydrochloride) as an almost white powder. 1H-NMR (400 MHz, CDCl3): delta=1.33 (d, J=6.8 Hz, 6H), 1.38 (d, J=6.1 Hz, 6H), 1.59-1-78 (m, 5H), 2.18 (s, 3H), 2.75-2.83 (m, 3H), 3.20-3.24 (m, 2H), overlaps 3.28 (sept, J=6.8 Hz, 1H), 4.56 (sept, J=6.1 Hz, 1H), 6.82 (s, 1H), 7.25-7.29 (m, 1H), 7.56 (br. s, 1H), 7.64 (m, 1H), 7.94 (m, 1H), 8.01 (br. s, 1H), 8.16 (br. s, 1H), 8.60 (m, 1H), 9.51 (br. s, 1H) ppm. 13C-NMR (100 MHz, CDCl3): delta=15.4, 18.9, 22.3, 33.9, 38.6, 47.5, 55.4, 71.4, 105.7, 111.0, 120.6, 123.1, 123.7, 124.9, 126.7, 127.3, 131.2, 134.7, 138.3, 138.5, 144.7, 155.3, 155.4, 157.5 ppm, Elemental analysis: calculated (%) for C28H36ClN5O3S: C 60.26, H 6.50, N 12.55, O 8.60 Cl 6.35, S 5.74, found: C 60.15, H 6.45, N 12.72, O 8.58, Cl 6.43, S 5.67.)

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, 761440-16-8, 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine.

Reference:
Patent; Novartis AG; Davis, Mark Clinton; Gong, Baoqing; Har, Denis; Kapferer, Tobias; Zheng, Xuchun; (25 pag.)US2020/39935; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

To a 1L glass vessel equipped with a stirrer and a thermometer probe were added the Formula ic (120 g, obtained by the Example-8b, Step-1), Water (1200 mL, 10.0 vol), Citric acid (73.50 g, 0.507 mol) at 25¡À5 C. The mass was cooled to 10¡À5 C under stirring. Aqueous Ammonia was added very slowly into the reaction mass at a constant rate under stirring. The reaction mass was warmed to 25¡À5 C, the solid material was filtered, washed with water (1000 mL, 10.0 vol) and dried at 55¡À5 C under vacuum to obtain to obtain Amorphous Dasatinib as a solid (94.5 g, 76.35% w.r.t. Formula II, 99.8% AUC, N-Oxide impurity:

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, 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; BIOCON LIMITED; BHAT, Ramakrishna, Parameshwar; RAGHUNADHACHETTY, Jithendrababu; KALIAPPAN, Mariappan; PALLE, Venkata, Raghavendracharyulu; REGALLA, VijayBhaskar, Reddy; (123 pag.)WO2019/8555; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products 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.

Synthesis of 3-(3-bromo-5-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA85); A solution of 2-(3-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (137 mg, 0.43 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (65 mg, 0.216 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 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 BA85 (28 mg, 36% yield). ESI-MS (M+H)+ m/z calcd 362.1, found 362.0.

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