Day: May 18, 2021

Reference of 5177-27-5, 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 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2,4-dichloropyrimidin-5-amine (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25% ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.

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 5177-27-5, 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; RATILAINEN, Jari; GOLDSTEINS, Gundars; WO2014/191632; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13223-25-1, 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 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

L-methyl lactate 0.46g (0.005 mol) and 2-Chloro-4,6-dimethoxy-pyrimidine 0.88g (0.005 mol) were dissolved in DMF 20 ml, K2CO3 0.52g (0.75 eq) was added thereto, and sodium methane sulfinate 0.1g was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and ethylacetate (EA) three times, and washed with brine twice, the organic layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 0.66g (54%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 1.63(d, 3H), 3.73(s, 3H), 3.89(s, 6H), 5.22(q, 1H), 5.72(s, 1H).

According to the analysis of related databases, 13223-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SNU R&DB Foundation; Korea Research Institute Of Chemical Technology; EP2497768; (2012); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13162-26-0, 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 13162-26-0 as follows.

Cyclopentylamine(5.2ml) and N,N-diisopropylethylamine(13.2ml) were dissolved into 150ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitro-6-methylpyrimidine(10.7g) in dichloromethane(30ml) at 0C. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for 1 hour. Purification was conducted by a column chromatography to obtain a bright-yellow solid(11.2g) in a yield of 84.8%. 1H NMR(400 MHz, CDCl3): delta 8.44(s, 2H), 4.41(m, 1H), 2.64(s,3H), 2.01-2.15(m, 2H), 1.61-1.76(m, 4H), 1.45-1.63(m, 2H)ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13162-26-0, its application will become more common.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 60025-09-4, 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 60025-09-4, name is 4-Amino-6-chloropyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To the solution of 44 (200 mg, 0.664 mmol, 1.1 eq) in t-BuOH(4 mL) were added 6-chloro-9H-purine (93 mg, 0.604 mmol, 1.0 eq)and DIPEA (149 mL, 0.906 mmol, 1.5 eq). The resultant mixture was stirred at 80 C under N2 atmosphere for 8 h and concentrated in vacuo. To the residue was added DCM, and the mixture was washed successively with saturated NaHCO3 solution, dilute hydrochloric acid (0.5 N) and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. Flash column chromatography utilizing EA/PE (1:1e3:1) and EA/AcOH (80:1) as the eluent afforded a light yellow oil. It was then dissolved in DCM, and the resulting solution was washed successively with saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, and concentrated in vacuo to afford 3-(1-((9H-purin-6-yl)amino)ethyl)-2-phenyl-2Hbenzo[e][1,2,4]thiadiazine 1,1-dioxide 55 as a light yellow solid.Yield 28%;

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 60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile.

Reference:
Article; Ma, Xiaodong; Wei, Jun; Wang, Chang; Gu, Dongyan; Hu, Yongzhou; Sheng, Rong; European Journal of Medicinal Chemistry; vol. 170; (2019); p. 112 – 125;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22536-61-4, 2-Chloro-5-methylpyrimidine, 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, 22536-61-4, blongs to pyrimidines compound. SDS of cas: 22536-61-4

2-Chloro-5-methyl-pyrimidine (18 mL, 151 mmol), potassium (Z)-but-2-en-2- yltrifluoroborate (commercially available from Sigma Aldrich, 31 g, 191 mmol), tricyclohexylphosphine (8.5 g, 30.2 mmol) and Pd2(dba)3 (13.82 g, 15.09 mmol) were added to a flask, which was then degassed and backfilled with nitrogen. To the flask was added 1,4-dioxane (252 mL) and aqueous potassium phosphate tribasic (37.5 mL, 453 mmol). The resulting reaction was heated at 100 C for 16 h. The reaction was then cooled to RT. The residue was filtered through a plug of silica gel and then loaded onto silica gel (0-20% EtOAc in heptanes) to afford (E)-2-(but-2-en-2-yl)-5-methylpyrimidine 27.01 (19 g, 125 mmol, 83% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-61-4, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; CHENG, Alan C.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; PATTAROPONG, Vatee; SWAMINATH, Gayathri; KREIMAN, Charles; MOEBIUS, David C.; SHARMA, Ankit; (543 pag.)WO2018/93580; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 2227-98-7, Adding some certain compound to certain chemical reactions, such as: 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine,molecular formula is C6H6N4, 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 2227-98-7.

[0088] (2R)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3- (pyrazin-2-ylsulfanyl)propan-l-ol (V.2). Compound V.l (0.220 g, 0.68 mmol) was dissolved in CH2CI2 (8 mL) and trifluoroacetic acid (2 mL) added. After 2 h the solvent was evaporated and the residue dissolved in MeOH (10 mL) and neutralized with Amberlyst A21 resin then passed through a short column of the same resin and eluted with MeOH. The fractions containing product were evaporated to a yellow gum that was dissolved in tert-butanol (4 mL) then aq. formaldehyde solution (37%, 0.061 mL, 0.81 mmol) and 9-deazaadenine (0.091 g, 0.68 mmol) were added and the mixture heated at 70 C for 16 h. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue chromatographed on silica gel (gradient of 10 – 15% 7M NH3/MeOH in CHCI3) to give V.2 as a colourless solid (0.055 g, 25%). XH NMR (500 MHz, CD3OD): delta 8.35 (d, J = 1.5 Hz, 1H), 8.28 (dd, J = 2.6, 1.7 Hz, 1H), 8.14 (d, J = 2.1 Hz, 1H), 8.12 (s, 1H), 7.43 (s, 1H), 4.05 (d, J = 13.9 Hz, 1H), 4.02 (d, J = 13.8 Hz, 1H), 3.74 (dd, J = 11.3, 4.9 Hz, 1H), 3.64 (dd, J = 11.3, 5.5 Hz, 1H), 3.39-3,31 (m, 2H + residual deuterated solvent), 3.01-2.97 (m, 1H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 158.2 (C), 152.0 (C), 150.8 (CH), 146.5 (C), 145.2 (CH), 144.6 (CH), 140.3 (CH), 129.0 (CH), 115.4 (C), 114.7 (C), 63.7 (CH2), 58.4 (CH), 41.4 (CH2), 31.6 (CH2). ESI-HRMS calcd Ci4H18N7OS+ (M+H)+, 332.1289, found 332.1287.

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. 2227-98-7, 4-Aminopyrrolo[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; SCHRAMM, Vern, L.; CLINCH, Keith; GULAB, Shivali, Ashwin; WO2015/123101; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 23002-51-9, 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. 23002-51-9, name is 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

Example 19 Methanesulfonyl-piperidin-4-yl)-(1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine To a stirred solution of (1-methanesulfonyl-piperidin4-yl)-(1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine (Example 18, 61 mg, 0.40 mmol) in DMF (2.5 mL), sodium bicarbonate (60 mg) and 1-methanesulfonyl-piperidin-4-ylamine(85 mg, 0.48 mmol) were added and the mixture was stirred at 100 C. for 5 hours. The solvent was removed under reduced pressure and the residue was treated with water and the mixture was extracted with EtOAc. The extract was dried with sodium sulfate and concentrated to give a solid, which was purified by reverse phase HPLC to give an off-white solid. 29 mg, 29%. MS (M+H)+, 297.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23002-51-9, 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Roberts, John Lawson; US2005/277655; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 90213-67-5, 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 90213-67-5, name is 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(2S,35)-ethyl 3 -aminobicyclo[2.2.2]octane-2-carboxylate hydrochloride (1.26 g, 5.40 mmol) and 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (1.10 g, 5.40 mmol) were dissolved in DMF (5 mL), then potassium carbonate (1.50 g, 11.00 mmol) was added. The mixture was stirred at rt overnight. Water (50 mL) was added to quench the reaction, and the resulting mixture was extracted with EtOAc (50 mL x 2). The combined organic phases were washed with saturated brine (80 mL), dried over anhydrous Na2504, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 10/1) to give the title compound as a yellow solid (979 mg, 50 %).MS (ESI, pos.ion) m/z: 363.2 [M+H]?H NMR (400 MHz, CDC13) (ppm): 6.87 (d, J= 3.4 Hz, 1H), 6.41 (s, 1H), 5.32 (s, 1H), 4.63 (s, 1H), 4.21 (q, J= 7.1 Hz, 2H), 3.76 (s, 3H), 2.39 (d, J 4.9 Hz, 1H), 1.96 – 1.52 (m, 1OH), 1.26 (t, J 7.0 Hz, 3H).

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 90213-67-5, 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; TANG, Changhua; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (215 pag.)WO2018/127096; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1114560-76-7, 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. 1114560-76-7, name is 4-Bromo-2-methylpyrimidine. A new synthetic method of this compound is introduced below.

Example 46a 6-Methoxy-5-(2-methyl-pyrimidin-4-yl)-pyridin-2-ylamine PdCl2(PPh3)2 (413 mg, 0.58 mmol) was added to a degassed mixture of 4-bromo-2-methyl-pyrimidine (1.02 g, 5.89 mmol), 6-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine 2 (Example 7c, 2.2 g, 8.79 mmol) and K2CO3 (2.43 g, 17.6 mmol) in a mixture of DME, EtOH and H2O (6:2:1, 200 mL). The reaction mixture was heated in a sealed tube for 1 hour at 100 C. The mixture was cooled to room temperature, diluted with ethyl acetate and filtered. The volatiles were removed in vacuo and the residue was purified by flash column chromatography using a gradient of 5 to 10% EtOAc in DCM to afford 610 mg (48%) of the title compound. 1H NMR (400 MHz, CD3OD) delta ppm 2.74 (s, 3H) 4.06 (s, 3H) 6.29 (d, 1H) 8.27 (d, 1H) 8.45 (d, 1H) 8.55 (d, 1H). ESMS m/z 217.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1114560-76-7, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2012/122843; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

A suspension of 4-chloro-7H-pyrrolo[2,3-d]pyri- midine (1.54 g, 10 mmol) and Pd(PPh3)4(ii6 mg, 0.100 mmol) in THF (10.0 mE, iM) was vacuum purged with N2. Then a solution of dimethylzinc (3.82 g, 40.0 mmol, 20.0 mE, 2M in toluene) was added and the mixture was vacuum flushed with N2 and then heated to 60 C. for 16 h. ECMSAPC1(+) showed .-i:i mixture of starting material to product. The reaction was heated to 80 C. for another 24 h, in which ECMS showed a 2: 1 mixture of product to starting material. The reaction mixture was cooled in an ice-water bath then quenched with saturated NaHCO3 (aq) and extracted with EtOAc. The EtOAc was washed with brine, dried with Mg504, filter and concentrated to an oil. The crude material was purified by ISCO-Rf on a 24 g column eluting with 0-100% EtOAc-Heptane to give compound V-1 (561 mg, 42%). ECMS [M+i] 134; ?HNMR (400 MHz, CDC13) oe ppm8.94 (s, iH), 7.42 (d, J=3.4 Hz, iH), 6.68 (d, J=3.4 Hz, iH),2.87 (s, 3H)

Statistics shows that 3680-69-1 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Pfizer Inc.; Tatlock, John Howard; McAlpine, Indrawan James; Tran-Dube, Michelle Bich; Rui, Eugene Yuanjin; Wythes, Martin James; Kumpf, Robert Arnold; McTigue, Michele Ann; (181 pag.)US2016/244475; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia