Day: June 16, 2021

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. 2380-63-4, name is 1H-Pyrazolo[3,4-d]pyrimidin-4-amine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2380-63-4

1H-[3,4-d]pyrazolopyrimidin-4-amine(5.3g, 39mmol) andN-Iodosuccinimide (13.3 g, 59 mmol) was suspended in N,N-dimethylformamide,The reaction was heated to 80C under a nitrogen atmosphere for 12 hours.After the reaction is completed, it is cooled to room temperature, water is added, and a large amount of solids are precipitated and filtered with a Buchner funnel.Solids in turn with saturated sodium thiosulfate solution,Water and hot ethanol are washed twice each.The oil pump was drained to give 7.8 g of the target compound in a yield of 77%.

The synthetic route of 2380-63-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Chen Deheng; Yan Ziqin; Guo Dexiang; (85 pag.)CN107759602; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 939986-65-9 , The common heterocyclic compound, 939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, 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.

The title compound (1-60) was prepared using the procedure for Example 17, using 4- hydroxy- 1H-indazole in Step 1. The free base form of the title compound was purified via silica gel (eluting with 1-20% MeOH in DCM) and then converted to the hydrochloride salt, using 2 M HC1 in ether. ?H NIVIR (300 IVIHz, DMSO-d6): 8.78 (s, 1H), 8.60 (br s, 3H), 7.77 (s, 1H), 7.48 (m, 1H), 7.35-7.45 (m, 2H), 6.94(m, 1H), 4.10-4.20(m, 2H).; A mixture of 6-hydroxyindole 1 (157 mg, 1.18 mmol), 6-chloropyrimidine-4-carbonitrile (150 mg, 1.07 mmol), K2C03 (444 mg, 3.21 mmol), DMF (2 mL), and THF (4 mL), was stirred at RT for 20 h. Additional 6-chloropyrimidine-4-carbonitrile (30 mg, 0.2 15 mmol) was added and the mixture stirred at RT for a further 16 h. The mixture was concentrated under reduced pressure. The residue was purified (silica gel; eluting 0 to 100% EtOAc in hexanes), to afford compound 2 (190 mg, 56%) as a yellow solid. LCMS Mass: 237.0 (M+1).To a stirred solution of compound 2 (40 mg, 0.169 mmol) in EtOAc (3 mL) and HOAc (0.3 mL) at RT, was added 10% Pd/C (10 mol%). The reaction mixture was stirred at RT under hydrogen (1 atmosphere pressure) for 1 h. The reaction mixture was filtered through a pad of celite, and the filtrate was concentrated under reduced pressure. The residue was purified via preparative HPLC (Waters XTerra Prep MS C-18 OBD 5 jiM 50 x 100mm column; eluting with 10-90% ACN/H20 containing 0.1% TFA, over 20 mm), followed by silica gel (eluting 0 to 100% EtOAc in hexanes), to afford compound 1-17 (3 mg, 7%) as a solid. ?H NIVIR (300 IVIFIz, MeOH-d4): 8.76 (m, 1H), 7.61 (m, 1H), 7.29 (m, 1H), 7.18 (m, 1H), 6.94 (m, 1H), 6.80 (m, 1H), 6.49 (m, 1H), 4.22 (s, 2H); LCMS Mass: 241.0 (M+1).

The synthetic route of 939986-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13479-88-4 , The common heterocyclic compound, 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, 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.

[00492] (+/-)-trans-Methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (284 mg, 1.55 mmol)and 5,7-dichlorothiazolo[5,4-d]pyrimidine (352 mg, 1.71 mmol) were dissolved in DMF (5 mL), then potassium carbonate (428 mg, 3.10 mmol) was added. The mixture was stirred at rt overnight. The reaction was stopped, and to the reaction mixture was added water (50 mL). The resulting mixture was extracted with ethyl acetate (50 mL x 2). The combined organic layers were washed with saturated brine (80 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to remove the solvent and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 10/1) to give the title compound as a yellow solid (317 mg, 58%).MS (ESI, pos.ion) m/z: 353.0 [M+H]1H NMR (600 MHz, CDC13) (ppm): 8.75 (s, 1H), 6.49 (d, J = 4.7 Hz, 1H), 4.63 (s, 1H), 3.76 (s, 3H), 2.50 (d, J= 5.6 Hz, 1H), 2.01 (d, J= 1.8 Hz, 1H), 1.95 (d, J= 2.5 Hz, 1H), 1.88- 1.76 (m, 2H), 1.73- 1.53 (m, 6H).

The synthetic route of 13479-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 935667-50-8, 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 935667-50-8 as follows.

To a -60 C solution of Example 361.0 (2.20 g, 6.3 mmol) in THF (13 mL) was added n-butyllithium (2.5 M solution in hexanes, 2.72 mL, 6.8 mmol) slowly via syringe. After 10 mm, a solution of Example 343.2 (660 mg, 5.2 mmol) in THF (5 mL) was added dropwise via cannula at-60 C. The resulting mixture was stirred at -60 C for 15 mm and was then allowed to warm to RT and stirred overnight. The reaction was quenched with saturated aqueous NH4C1 and extracted with EtOAc (3X). The combined organic layers were dried over anydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (eluent was 20-70% EtOAc in hexanes over 30 mm) to provide Example 355.01 (547 mg, 22% yield) as a red solid. LCMS-ESI (pos.) m/z: 498.0 (M+Na).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,935667-50-8, its application will become more common.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 852180-74-6, Adding some certain compound to certain chemical reactions, such as: 852180-74-6, name is 3-(Pyrimidin-5-yl)benzoic acid,molecular formula is C11H8N2O2, 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 852180-74-6.

A mixture of 3-pyrimidin-5-yl-benzoic acid (100 mg, 0.50 mmol) and SOCl2 (73 mu, 1.0 mmol) was heated under reflux for 4 h. The solvent was evaporated off under reduced pressure and the residue was dissolved in DCM (5 mL) and slowly added to a mixture of 4- (chlorodifluoromethoxy)aniline (106 mg, 0.55 mmol) and TEA (140 mu, 1.0 mmol) in DCM (5 mL). The mixture was stirred at RT overnight. The solvent was evaporated off under reduced pressure and the residue was suspended in EtOAc (10 mL),filtered through a 10 muetaiota Isolute fritted cartridge and the filtrate was evaporated to dryness under reduced pressure to give the crude product which was purified by preparative HPLC to afford the title compound. LC-MS (Condition 4) tR = 1.15 min, m/z = 375.8 [M+H]+; XH-NMR (400 MHz, DMSO-d6) delta ppm 7.40 (d, J = 9.05 Hz, 2 H) 7.73 (t, J = 7.82 Hz, 1 H) 7.92 (m, 2 H) 8.06 (t, J = 6.97 Hz, 2 H) 8.37 (t, J = 1.96 Hz, 1 H) 9.24 – 9.29 (m, 3 H) 10.52 (s, 1 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. 852180-74-6, 3-(Pyrimidin-5-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; MOUSSAOUI, Saliha; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; WO2013/171641; (2013); 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. 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

To a stirred solution of 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (3.5 g, 15.02 mmol, 1 equiv) in DMF (60 mL) was added sodium hydride (0.72 g, 18.02 mmol, 1.2 equiv) at 0C. The reaction mixture was stirred for 15 mm at 0C. Methyl iodide (1.12 mL, 18.02 mmol, 1.2 equiv) was added to the reaction mixture at 0C. The reaction mixture was warmed to room temperature and stirred for 3h. The reaction mixture was quenched with ice water and extracted in ethyl acetate. The organic layer was dried over sodium sulphate and evaporated to obtain crude product, which was purified over silica gel flash column chromatography. The compound eluted out in 30% EtOAc in n-Hexane. Fractions obtained were concentrated to give 3-bromo-4-chloro- 1-methyl-i H-pyrazolo[3,4- d]pyrimidine (2.0 g, 57%) as pale yellow solid. LCMS (ES) m/z = 247.4, 249.4 [M+H. ]. 1H NMR (400 MHz, DMSO-d6) O ppm -4.03 (5, 3H), 8.88 (5, 1H)

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, 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); 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. 31169-25-2, name is 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 31169-25-2

Dimethylformamide (25.8 mL, 0.33 mol) and dichloromethane (150 mL) were added to a reactor. Oxalyl chloride (46.4 mL, 0.53 mol) diluted with dichloromethane (150 mL) at room temperature was added to the reactor for about 30 minutes. 7-bromothieno[3,2- d]pyrimidin-4(3H)-one (35 g, 0.15 mol) was added thereto, and then, the reaction solution was heated to reflux for 3 hours. The temperature of the reaction solution was lowered and water was carefully added thereto. The organic layer was separated, and the aqueous layer was subjected to extraction using dichloromethane. The extracted organic layer was dried over anhydrous sodium sulfate. The dried organic layer was filtered and distilled under reduced pressure, and dried with nitrogen gas to obtain the title compound (30.5 g, 85percent). 1H-NMR Spectrum (300 MHz, DMSO-: delta 9.16 (s, 1H), 8.79 (s, 1H)

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, 31169-25-2, 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one.

Reference:
Patent; HANMI PHARM CO., LTD.; BAE, In Hwan; SON, Jung Beom; HAN, Sang Mi; KWAK, Eun Joo; KIM, Ho Seok; SONG, Ji Young; BYUN, Eun Young; JUN, Seung Ah; AHN, Young Gil; SUH, Kwee Hyun; WO2013/100632; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 56844-12-3, 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 56844-12-3, name is 6-Bromo-4-chlorothieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 6-Bromo-4-chlorothieno[2,3-d]pyrimidine(5a) (200 mg, 0.802 mmol) was mixed with 1-phenylethanol (2a) (118 mg, 0.962 mmol), Cs2CO3( 313 mg, 0.962 mmol) and acetonitrile (2 mL). The reaction was then stirredunder nitrogen atmosphere at reflux and followed by GC. The mixture was cooledto rt, diluted with EtOAc (40 mL), washed with sat. aq. KHCO3 (20mL), water (2×20 mL) and brine (30 mL). The combined organic fractions weredried over Na2SO4 and concentrated in vacuum. Crudeproduct was absorbed onto Celite 545 and purified by silica gel columnchromatography (n-pentane/EtOAc,6/1). This gave 245 mg (0.730 mmol, 91%) of 6a as an off-white 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 56844-12-3, 6-Bromo-4-chlorothieno[2,3-d]pyrimidine.

Reference:
Article; Han, Jin; Sundby, Eirik; Hoff, Bage H.; Journal of Fluorine Chemistry; vol. 153; (2013); p. 82 – 88;,
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.1683-75-6, name is 2-Amino-4-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, molecular weight is 147.54, as common compound, the synthetic route is as follows.Formula: C4H3ClFN3

[00306] A mixture of 4-chloro-5-fluoropyrimidin-2-amine (3) (O. lg, 0.64 mmol) and 3,4- dichlorophenyl isocyanate (0.24g, 1.29 mmol) in dioxane (3 mL) was heated overnight at 90 C. The mixture was chromatographed in 0-60% ethyl acetate in hexanes to afford the title product (167). (75mg, 35%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1683-75-6, 2-Amino-4-chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CURTANA PHARMACEUTICALS, INC.; BEATON, Graham; MCHARDY, Stanton F.; LOPEZ JR., Ambrosio; CAMPOS, Bismarck; WANG, Hua-Yu Leo; (143 pag.)WO2019/169112; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1211443-61-6, 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 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a suspension of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (5) (586 mg, 2 mmol) in 20 mL 1,4-dioxane were added compound 3a-f, 3i-u(2 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), BINAP (62 mg, 0.1 mmol) and Cs2CO3 (978 mg, 3 mmol) and the flask was purged with Ar. Then the flask was sealed and the mixture was heated for 12 h at 100. The reaction was cooled to rt, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4a-f, 4i-o, 4r-u.

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 1211443-61-6, 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide.

Reference:
Article; Li, Yongtao; Guo, Qingxiang; Zhang, Chao; Huang, Zhi; Wang, Tianqi; Wang, Xin; Wang, Xiang; Xu, Guangwei; Liu, Yanhua; Yang, Shengyong; Fan, Yan; Xiang, Rong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3231 – 3237;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia