Category: pyrimidines

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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide, the common compound, a new synthetic route is introduced below. Quality Control of 2-Chloropyrimidine-4-carboxamide

A mixture of 3-{[2-amino-6-(3-chloro-2-methylphenyl) pyrimidin-4-yl]ami no}propan1-01 (intermediate 24), 2-chloropyrimidine-4-carboxamide (1.1 equiv.) and 0s2003(2.0 equiv.) in DMSO was heated in a sealed tube at 90C for 2 h. After coolingwas methanol added to the solution, followed by filtration and purification by preparative LC to furnish the title compound. LCMS [M+H]414. 1H NMR (400MHz, METHANOL-d4) oe ppm 8.79 (d, J=5.1 Hz, 1 H), 7.69 (s, 1 H), 7.55 – 7.63(m, 1 H), 7.30 – 7.41 (m, 3 H), 6.04 (s, 1 H), 4.59 (t, J=6.0 Hz, 2 H), 3.76 (t, J=6.8Hz, 2 H), 2.18 (quin, J=6.3 Hz, 3 H).

The synthetic route of 22536-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; JACQUES, Sylvain; HOMAN, Evert; HELLEDAY, Thomas; WO2015/187088; (2015); A1;,
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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. 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine, the common compound, a new synthetic route is introduced below. name: 4,6-Dichloro-2-methylpyrimidin-5-amine

Preparation 1 6-Chloro-N*4*-(4-methoxyphenyl)-2-methylpyrimidine-4,5-diamine; 4,6-dichloro-2-methyl-pyrimidin-5-ylamine (985.3 g, 5.53 MoI) was added with stirring to a 2OL reactor charged with EtOH (4.0 L) over 3 minutes to give complete solution. p-Anisidine (718.0 g, 5.83 MoI) was then added with stirring over 3 minutes. A dark brown solution was observed and addition of both reagents gave an exotherm of 130C. EtOH (1 L) was then added followed by a premixed solution of c.HCI (0.5 L) in EtOH (2 L) at a steady rate over 40 minutes. A slight exotherm up to approx 2O0C was noted. The solution was then warmed to 8O0C and held at that temperature for 3.5 hours during which a grey precipitate appeared. Heating was continued for a further 2 hours then the temperature was reduced to 490C, and stirring was continued for 19 hours. The reaction mixture was allowed to cool to 3O0C, before draining out of 2OL reactor. The reaction mixture was filtered to collect a beige precipitate. Washed with EtOH (2.5 L), the MTBE (2.5 L) and sucked dry under N2(g) for 22 hours. The filter cake was then dried under vacuum at 5O0C for 60 hours, to yield title compound, as the hydrochloride salt, as a beige solid (1.465 Kg, 88%). 1H NMR (400MHz, DMSO-d6) delta = 2.27 (s, 3H), 3.71 (s, 3H), 6.90 (d, 2H), 7.58 (d, 2H), 9.10 (bs, 1 H). LCMS (System 4): 2.4 mins m/z (APCI) 265 [MH+]

The synthetic route of 39906-04-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; WO2009/144632; (2009); A1;,
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Related Products of 49845-33-2, 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 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A heterogeneous solution of 2.4-dichloro-5-nitro-pyrimidine (1.0 eq.) and iron (6.0 eq) in acetic acid, at a concentration of 0.4 M, was stirred vigorously for 14 hours. The mixture was then passed through a celite pad, eluting with MeOH. Upon removal of the volatiles in vacuo, the residue was dissolved in EtOAc, washed with Na2CO3(sat.), NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding 2,4-dichloropyrimidin-5-amine (80%). LCMS (m/z): 157.0 (MH+); LC Rt=1.85 min.

According to the analysis of related databases, 49845-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Burger, Matthew; Lindvall, Mika; US2011/195980; (2011); A1;,
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Synthetic Route of 42754-96-1, 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 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

4,6-dichloro-1H-pyrazolo[3,4-djpyrimidine (2.50 g, 13.23 mmol) was added to a flask and dissolved in 1,4-dioxane (52.9 ml). p-Toluenesulfonic acid monohydrate (pTsOH, 0.25 g, 1.32 mmol) was then added to the clear, pale yellow solution followed by 3,4-dihydro-2h-pyran (1.8 ml, 19.84 mmol) and the reaction was heated to 40 C andstirred overnight. The resulting mixture was then cooled and concentrated in vacuo. The cmde was purified by flash column chromatography using a 0-100% EtOAc:hexanes gradient to yield 4,6-dichloro- 1 -(tetrahydro-2H-pyran-2-yl)- 1H-pyrazolo[3 ,4- djpyrimidine (2.6 g, 9.52 mmol, 72.0 % yield). (m/z,): [M+Hj calculated for C10H10C12N4O 274.0 found 188.9 (loss of THP fragment).

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 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FENSTER, Erik; LAM, Tom M.; LOO, Mandy; MCKINNELL, Robert Murray; PALERMO, Anthony Francesco; WANG, Diana Jin; FRAGA, Breena; NZEREM, Jerry; DABROS, Marta; THALLADI, Venkat R.; RAPTA, Miroslav; (217 pag.)WO2019/27960; (2019); A1;,
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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 2434-53-9, name is 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 2434-53-9

General procedure: A mixture of isatin 1 (1 mmol), 1,3-indandion 2 (1 mmol), aminouracil 3 (1 mmol) andSBA-oxime-Zn (0.1 g) was heated in refluxing water(5 mL) for appropriate time (Table 1). The reactionwas monitored by TLC (n-hexane-ethyl acetate 1:1),and after completion of the reaction, the reactionmixture was filtered for separation of solid productand catalyst from water. The remaining solid waswashed with ethanol (2×10 mL) for separation ofthe product from the catalyst. Finally, the productwas purified by recrystallization in hot EtOH. The desired pure products were characterized bycomparison of their melting point data with literature.All the products are known compoundsand their melting points are compared with reportedvalues [14]. Some selected samples were alsocharacterized by IR and NMR spectroscopic data.

With the rapid development of chemical substances, we look forward to future research findings about 2434-53-9.

Reference:
Article; Ghorbani, Sayed Hosein; Hashemi, Mohammad Mahmoodi; Oriental Journal of Chemistry; vol. 31; (2015); p. 181 – 188;,
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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. 1004-40-6, name is 6-Amino-4-hydroxy-2-mercaptopyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 1004-40-6

General procedure: A mixture of aminouracil (1 mmol), isatin (1 mmol), and carbonyl compound (1 mmol) in DES (1 ml) was stirred on magnetic stirrer at 70oC for nearly 35-55 min. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured on crushed ice.The DES remained in water and solid product was separated by filtration. The DES was recovered from the filtrate by evaporation. The recovered DES was reused three-four times with comparable yields.

The synthetic route of 1004-40-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khandelwal, Sarita; Rajawat, Anshu; Tailor, Yogesh Kumar; Kumar, Mahendra; Combinatorial Chemistry and High Throughput Screening; vol. 17; 9; (2014); p. 763 – 769;,
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Reference of 180869-36-7, Adding some certain compound to certain chemical reactions, such as: 180869-36-7, name is 4-(Dimethoxymethyl)-2-(methylthio)pyrimidine,molecular formula is C8H12N2O2S, 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 180869-36-7.

Example 29A (14.6 g) was dissolved in methanol (122 mL) and water (122 mL) and the stirring mixture was cooled with an ice bath then oxone (potassium peroxomonosulfate) (67.2 g) was added portionwise over 15 minutes. The resulting mixture was stirred at 0 C for 3 hours, and the cooling bath was removed to allow for the reaction to stir at room temperature for an additional 2 hours. The mixture was concentrated to remove most of the methanol and the remaining aqueous mixture was filtered and washed with ~200 mL of methylene chloride. The biphasic mixture was poured into a separatory funnel, the organic layer was removed and the aqueous layer was washed with one portion of methylene chloride. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated onto silica gel. Purification by flash chromatography on a CombiFlash Teledyne Isco system using a Teledyne Isco RediSep Rf gold 330 g silica gel column (eluting 50-100% ethyl acetate/heptane) afforded the title compound. MS (APCI) m/z 233.3 (M+H)+.

According to the analysis of related databases, 180869-36-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; BRAJE, Wilfried; DOHERTY, George; JANTOS, Katja; JI, Cheng; JUDD, Andrew; KUNZER, Aaron; MASTRACCHIO, Anthony; SONG, Xiaohong; SOUERS, Andrew; SULLIVAN, Gerard; TAO, Zhi-Fu; LAI, Chunqui; KLING, Andreas; POHLKI, Frauke; TESKE, Jessc; WENDT, Michael; BRADY, Patrick; WANG, Xilu; PENNING, Thomas; MICHAELIDES, Michael; (448 pag.)WO2019/35927; (2019); A1;,
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Application of 4595-60-2, 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 4595-60-2 as follows.

General procedure: A magnetic stirring bar, nanocrystalline CuO (10 mg, 3 mol %), KOH (112 mg, 2 mmol) and phenol/substituted phenol/ thiophenol (1.2 mmol) were added into an oven-dried flask (25 mL). The flask was sealed with a septum, followed by three cycles of evacuation and filling with dry nitrogen. Then aryl halide (1 mmol) and N,N-dimethyl acetamide (DMAc) (4 mL) were injected through a syringe. The flask was sealed and stirred under nitrogen until the completion of the reaction (as monitored by TLC or GC). The catalyst was recovered from the reaction mixture and washed several times with ethyl acetate. The catalyst-free reaction mixture was quenched with brine solution and the product was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate, 80/20) to afford the product with high purity.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-60-2, its application will become more common.

Reference:
Article; Babu, S. Ganesh; Karvembu; Tetrahedron Letters; vol. 54; 13; (2013); p. 1677 – 1680;,
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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.137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, molecular formula is C15H14N4O3, molecular weight is 298.3, as common compound, the synthetic route is as follows.HPLC of Formula: C15H14N4O3

To a solution of pemetrexed-fragment 2 (60mg, 0.2mmol) and amine SDC-TRAP-0004 (82mg, 0.2mmol) in anhydrous DMF (3 mL) was added EDC (60mg, 0.3mmol). The reaction mixture was stirred at room temperature for 18h. The reaction mixture was then diluted with water (5 mL) and extracted with ethyl acetate (lOOmL). The organic phase was dried with sodium sulfate, filtered and evaporated, followed by flash chromatography (hexane-ethyl acetate 1:1 and ethyl acetate-methanol 98:2) to give SDC-TRAP-0019 (95mg, 70%) as a white solid 4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)- N-(2-(5-(3-(2,4-dihydroxy-5-isopropylphenyl)-5-hydroxy-4H-1,2,4-triazol-4-yl)-1H-indol- 1-yl)ethyl)-N-methylbenzamide 1H NMR (400 MHz, DMSO-d6) : 11.86 (s, 111); 10.61(s, 111); 10.14(s,1H);9.51 (s, 111); 9.47 (s, 111); 7.59-7.45 (m, 211); 7.28-6.96 (m, 511); 6.72 (m, 211);6.47(s,1H); 6.32 (s, 111); 6.24 (s, 111); 6.00( bs, 211); 4.46-4.28 (m,2H);3.75-3.49(m,2H); 2.96 -2.80(m, 511); 2.61(s, 311); 0.81 (d, J = 6.9 Hz, 611).ESMS calculated for C371137N905: 687.29; Found: 688.2 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; CHIMMANAMADA, Dinesh, U.; YING, Weiwen; (368 pag.)WO2015/143004; (2015); A1;,
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Electric Literature of 353272-15-8, 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.353272-15-8, name is 6-Chloro-5-iodopyrimidin-4-amine, molecular formula is C4H3ClIN3, molecular weight is 255.4442, as common compound, the synthetic route is as follows.

To a mixture of 6-chloro-5-iodopyrimidin-4-am.ine (500 mg, 0.196 mmol), Pd(PPh3)2Cl2 (69 mg, 0.10 mmol ) and Cul (19 mg, 0.10 mmol) under 2 atmosphere were added a solution of etiiynyltrimethylsilane (1 ,38 mL, 9.79 mmol) in DMF (1.5 mL) and a solution triethylamine (0.54 mL, 3.91 mmol) in DMF (1.5 mL), The resulted mixture was heated to 47 C and stirred further for 2 hours. The mixture was diluted with EtOAc (30 mL), and the resulted mixture was washed with water (20 mL x 2) and brine (20 mL). The separated organic phase was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) ::: 10/1) to give the title compound as a brown solid (442 mg, yield 100%). MS (ESI, pos. ion) m/z: 226.0 [M+H]+; NMR (400 MHz, CDCb) delta (ppm): 8.31 (s, 1H), 5.62 (s, 2H), 0.31 (s, 9H).

Statistics shows that 353272-15-8 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-5-iodopyrimidin-4-amine.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); A1;,
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