Category: pyrimidines

Application of 257280-25-4, 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.257280-25-4, name is 5-Bromo-2-phenoxypyrimidine, molecular formula is C10H7BrN2O, molecular weight is 251.08, as common compound, the synthetic route is as follows.

Synthesis of 2-(2-chloro-6-fluorophenyl)-5-(2-phenoxypyrimidin-5-yl)- lH-imidazole-4-carbonitrile (EX-43)[000265] A solution of 5-bromo-2-phenoxypyrimidine (1-28) (0.3 mmol) and hexamethylditin (0.3 mmol) in DME (3 mL) was degassed with nitrogen for 5 minutes. Pd(PPh3 )4 (0.015 mmol) was added and the reaction was heated at 80 0C for 12 hours. The reaction was subsequently cooled to room temperature and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and reduced to dryness. The crude product was purified by flash column chromatography (hexanes : EtOAc = 9 : 1) to afford 5-(trimethylstannyl)-2-phenoxypyrimidine (1-29) as a clear oil. MS (m/z) (M+l)+: 335.0, 337.0. [000266] 5-(Trimethylstannyl)-2-phenoxypyrimidine (1-29) (0.16 mmol) and 5-bromo-2- (2-chloro-6-fluorophenyl)-lH-imidazole-4-carbonitrile (1-10) (0.083 mmol) were dissolved in DME (2 mL) and degassed for 5 minutes with nitrogen. Pd(PPh3)4 (0.0082 mmol) was added and the reaction was heated at 85 0C for 12 hours. The reaction was cooled to room temperature and partitioned with EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and reduced to dryness. The crude product was purified by flash column chromatography (hexanes : EtOAc = 3 : 1) to afford 2-(2-chloro-6- fluorophenyl)-5-(2-phenoxypyrimidin-5-yl)-lH-imidazole-4-carbonitrile (EX-43) as white glassy solid. 1U NMR (400MEtaz, d4-MeOO) delta 8.95 (s, 2H), 7.50 (m, IH), 7.37 (m, 3H), 7.21 (m, 2H), 7.14 (m, 2H). MS (m/z) (M+l)+: 392.5.

Statistics shows that 257280-25-4 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-phenoxypyrimidine.

Reference:
Patent; IRM LLC; CHIANELLI, Donatella; MOLTENI, Valentina; ALBAUGH, Pamela A.; CHOI, Ha-Soon; LOREN, Jon; WANG, Zhicheng; MISHRA, Pranab; WO2010/127152; (2010); A2;,
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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.10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine, molecular formula is C8H9Cl2N3O, molecular weight is 234.08, as common compound, the synthetic route is as follows.Safety of 4-(4,6-Dichloropyrimidin-2-yl)morpholine

Step 1: A mixture of 2,2-dimethylmorpholine (2.0 equiv.), 4-(4,6-dichloropyrimidin-2-yl)morpholine (1 equiv.) and triethylamine (6 equiv.) in EtOH (0.2 M) were heated to 110 C. for 25 min in the microwave. The reaction mixture was partitioned between EtOAc and water. The organic phase was dried over sodium sulfate. The resulting solution was concentrated and dried under vacuo to give 4-(6-chloro-2-morpholinopyrimidin-4-yl)-2,2-dimethylmorpholine and was used in the next step without further purification. LCMS (m/z) (M+H)=313.2, Rt=0.86 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10397-13-4, 4-(4,6-Dichloropyrimidin-2-yl)morpholine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; Barsanti, Paul A.; Burger, Matthew; Lou, Yan; Nishiguchi, Gisele; Polyakov, Valery; Ramurthy, Savithri; Rico, Alice; Setti, Lina; Smith, Aaron; Taft, Benjamin; Tanner, Huw; DiPesa, Alan; Yusuff, Naeem; US2014/275003; (2014); A1;,
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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. 39551-54-7, name is 2,4-Dichloropyrido[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below., Product Details of 39551-54-7

Compound 94j (195.7 mg, 0.798 mmol) was dissolved in 4M HCl in dioxane (3 mL) and stirred at rt for 1 h. The reaction mixture was then concentrated in vacuo. The residue was treated with 2-methyltetrahydrofuran (5 mL), 2,4-dichloropyrido[3,2-d]pyrimidine (160 mg, 0.525 mmol) and N,N-diisopropylethylamine (0.57 mL, 3.272 mmol) and heated with an 80 C. bath for 3 h. The reaction mixture was cooled to rt, concentrated under reduced pressure and the residue was subjected to silica gel chromatography eluting with 0-100% EtOAc in hexanes to obtain compound 96a as a mixture of two diastereomers (2:3 ratio). LCMS-ESI+ (m/z): [M+H]+ calculated for C15H22ClN4O: 309.15. found: 309.08; TR=1.41 min on LC/MS Method A.

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, 39551-54-7, 2,4-Dichloropyrido[3,2-d]pyrimidine.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Mackman, Richard L.; Metobo, Samuel E.; Mish, Michael R.; Pyun, Hyung-jung; Zablocki, Jeff; (175 pag.)US2016/289229; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, 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, Product Details of 148550-51-0, blongs to pyrimidines compound. Product Details of 148550-51-0

Stage 1 – Coupling; Piperidin-4yl-methanol (2.48g, 21.55mmol) was stirred in 1 :1 DMF/MeCN (2OmL) with K2CO3 (8.9g, 64.65mmol) for 10 minutes at RT under a nitrogen atmosphere. Intermediate F (5g, 21.55mmol) was then added and the reaction allowed to stir for 20 minutes. It was then diluted with H2O (10OmL) and extracted with EtOAc (2 x 10OmL). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to give the product as an orange solid which was used in the next step without further purification (5.7Og, 99percent). m/z = 266 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; CHROMA THERAPEUTICS LTD.; WO2008/53131; (2008); A1;,
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Electric Literature of 3438-48-0, 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.3438-48-0, name is 4-Phenylpyrimidine, molecular formula is C10H8N2, molecular weight is 156.18, as common compound, the synthetic route is as follows.

General procedure: A mixture of a 4-substituted pyrimidine (2 mmol), 0.53 g3-(2-bromoacetyl)-2H-chromen-2-one (2 mmol), and anactivated alkyne (2.5 mmol) in 40 cm3 1,2-epoxybutanewas heated at reflux temperature for 24 h. The solvent waspartly removed under vacuum, 10 cm3 of MeOH wasadded and the mixture was left overnight at room temperature.The solid formed was filtered, washed on the filterwith a mixture of MeOH/diethyl ether 1:1 and crystallizedfrom CHCl3/MeOH. Ethyl 3-phenyl-7-(2-oxo-2H-chromen-3-yl)-carbonylpyrrolo[1,2-c]pyrimidine-5-carboxylate(13, C26H18N2O5)Yellow crystals; yield: 0.51 g (58 %); m.p.: 273-275 C; 1HNMR (CDCl3 ? TFA, 300 MHz): d = 1.48 (t, J = 7.1 Hz,3H, CH3), 4.52 (q, J = 7.1 Hz, 2H, CH2), 7.49-7.54, 7.63-7.65, 7.77-7.90 (3 m, 9H, 5 H-Phenyl, 4 H-Coum), 8.39 (s,1H, H-6), 8.45 (s, 1H, H-Coum), 8.61 (s, 1H, H-4), 11.29 (s,1H, H-1) ppm; 13C NMR (CDCl3 ? TFA, 75 MHz):d = 14.2 (CH3), 63.1 (CH2), 112.1 (C-4), 117.4 (C-Coum),126.5 (C-Coum), 127.5, 130.2, 132.6 (C-20, C-30, C-40, C-50C-60), 130.3, 133.9, 135.7 (C-6, 2 C-Coum), 110.5, 118.2,123.9, 124.4, 131.4, 140.1, 145.9, 154.6 (C-3, C-4a, C-5, C-7, C-10, 4 Cq-Coum), 143.9 (C-1), 148.9 (C-Coum), 164.0(CO2Et), 180.4 (CO-Coum) ppm; IR (KBr): v = 1728,1698, 1630, 1613, 1525, 1477, 1355, 1258, 1210 cm-1.

Statistics shows that 3438-48-0 is playing an increasingly important role. we look forward to future research findings about 4-Phenylpyrimidine.

Reference:
Article; Popa, Marcel M.; Georgescu, Emilian; Draghici, Constantin; Georgescu, Florentina; Dumitrascu, Florea; Dumitrescu, Denisa; Monatshefte fur Chemie; vol. 146; 12; (2015); p. 2029 – 2040;,
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Reference of 16357-69-0, 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 16357-69-0 as follows.

General procedure: To the solution of corresponding quinazolone intermediate 13a(13b, 13c or 13d) in DCM (4 mL/1 mmol substrate)was added TFA (1mL/1 mmol substrate) dropwise at 0 C, and the resultant mixturewas stirred at room temperature. After 13a (13b, 13c or 13d) wastotally consumed, saturated NaHCO3 solution was added dropwiseat 0 C to adjust the PH value to 7. Following extraction with DCM,the organic layer was washed with brine, dried over anhydrousNa2SO4, and concentrated in vacuo to afford the Boc-deprotectedsecondary amine as slightly yellow solid.The mixture of corresponding Boc-deprotected secondaryamine (1.0 eq), 6-chloro-9H-purine (1.5 eq), DIPEA (4.0 eq) and t-BuOH (15 mL/1 mmol secondary amine) was stirred at 80 C underN2 atmosphere. After the secondary aminewas totally consumed, t-BuOH was removed in vacuo, and the residue was dissolved inDCM. The solution was washed with saturated NaHCO3 solution,dried over anhydrous Na2SO4, and concentrated in vacuo. Finally,the crude product underwent flash column chromatography (DCM/EA 5:1-1:1, V/V) to afford the purine derivative (14 or 15e17) aspale solid. Compounds with 4-aminopyrimidine-5-carbonitrile, 2-amino-6-methylpyrimidine-5-carbonitrile, 2-fluoro-9H-purine or2-chloro-9H-purine as HBs were prepared via similar procedure tothat for 14e17. However, the eluents utilized in the final flash columnchromatography of 21, 22, 24, 25 and 27 were different (DCM/EA 15:1-5:1, V/V, for 21, 24 and 27; DCM/EA 20:1-8:1, V/V, for22 and 25). The NMR spectra of 14e17, 28 and 29 indicated theexistence of rotamers.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16357-69-0, its application will become more common.

Reference:
Article; Tao, Qiangqiang; Chen, Yuqing; Liang, Xiao; Hu, Yongzhou; Li, Jiaming; Fang, Fang; Wang, Huchuan; Meng, Chang; Liang, Jingtai; Ma, Xiaodong; Gui, Shuangying; European Journal of Medicinal Chemistry; vol. 191; (2020);,
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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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. name: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine was dissolved in 57 wt. % hydriodic acid in H2O. The solution was stirred for 48 h at room temperature, and the solid was removed by filtering. The suspension in cold water was brought to pH 8 with NH3 (aq) solution. The solid was filtered, washed with water and dried.

The synthetic route of 3680-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lee, Sun-Mi; Yoon, Kyoung Bin; Lee, Hyo Jeong; Kim, Jiwon; Chung, You Kyoung; Cho, Won-Jea; Mukai, Chisato; Choi, Sun; Kang, Keon Wook; Han, Sun-Young; Ko, Hyojin; Kim, Yong-Chul; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5036 – 5046;,
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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 108381-23-3, name is Ethyl 2-chloro-4,6-dimethylpyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Ethyl 2-chloro-4,6-dimethylpyrimidine-5-carboxylate

Step 3. Synthesis of ethyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)-4,6-dimethylpyrimidine-5-carboxylate, 6c 1,8-diazabicyclo[5.4.0]undec-7-ene (1.086 g, 7.15 mmol) was added to a mixture of 6b (1.02 g, 4.75 mmol) and 1,2,3,4-tetrahydroisoquinoline (0.95 g, 7.13 mmol) in DMSO (5 ml) at 0 C. over 5 minutes. The mixture was stirred for an additional 5 minutes at room temperature. The mixture was washed with brine, extracted with ethyl acetate and chromatographed to yield 6c (1.43 g, 4.5 mmol, 95%).

With the rapid development of chemical substances, we look forward to future research findings about 108381-23-3.

Reference:
Patent; VALEANT PHARMACEUTICALS INTERNATIONAL; US2008/318979; (2008); A1;,
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Related Products of 56844-38-3, 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.56844-38-3, name is 2,4-Dichloro-5-methylthieno[2,3-d]pyrimidine, molecular formula is C7H4Cl2N2S, molecular weight is 219.09, as common compound, the synthetic route is as follows.

EXAMPLE 78 Following the procedure of Example 1, the reaction of 3,4-methylenedioxyphenethylamine with 2,4-dichloro-5-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-5-methyl-4-(3,4-methylenedioxyphenethylamino)-thieno-[2,3-d]-pyrimidine

Statistics shows that 56844-38-3 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-5-methylthieno[2,3-d]pyrimidine.

Reference:
Patent; Cell Pathways, Inc.; US6133271; (2000); A;,
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Pyrimidine – Wikipedia

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 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

A solution of 56b (20 g, 86 mmoi) in thy ACN (300 mL) under nitrogen was charged with iV,O-Bistrimethyisiiyi)acetamide (19.3 g, 95 mmol) then stirred at RT for 30 mm. The mixture was then charged with I -O-acetvl-2.3.5-tri-O-benzoyl-13-d-ribofiiranose (56c) (48.1 g, 78 mmol) and TMSOTf(21 g, 78 mmol) and stirred at RT for 30 mm. The mixture was then heated and stirred at 80 C for 5 h. The reaction mixture was cooled to RI, diluted with EtOAc (1 IL) washed with sat. sodium bicarbonate (ilL), brine (1 IL), dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure and purified by FCC (Si02, 15% EtOAc in hexanes) to afford 56d (31.4 g, 40.1 mmol, 51% yield) as a white solid foam. LCMS purity:86.5%; LRMS (ES1) m/z caicd for [M+H]?: 676.05/678.05. Found: 676.05/678.05.

With the rapid development of chemical substances, we look forward to future research findings about 22276-95-5.

Reference:
Patent; PRELUDE THERAPEUTICS, INCORPORATED; LUENGO, Juan; LEAL, Raul, A.; LIN, Hong; SHETTY, Rupa; (166 pag.)WO2018/85833; (2018); A2;,
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