Pyrimidines

Application of 56621-89-7, 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.56621-89-7, name is 5-Amino-2-methoxypyrimidine, molecular formula is C5H7N3O, molecular weight is 125.1286, as common compound, the synthetic route is as follows.

Step 1. l-(4-Bromophenyl)-N-(2-methoxypyrimidin-5-yl)cyclobutane-l- carboxamide: Into a 200 mL round bottom flask equipped with a magnetic stir bar and under N2 was added 2-methoxypyrimidin-5-amine (1.23 g, 9.80 mmol) and l-(4-bromophenyl)cyclo- butanecarboxylic acid (2 g, 7.84 mmol). The solids were dissolved in EtOAc (20 mL) and treated with pyridine (1.24 g, 15.68 mmol, 1.27 mL) followed by propylphosphonic anhydride (7.48 g, 1 1.76 mmol, 6.99 mL, 50% purity) in EtOAc. The yellow-orange solution was stirred at 24 C for 5 hr, the reaction was worked up by adding HC1 ( 1M, 20 mL). The EtOAc layer was concentrated and purified by column chromatography eluting with 10% to 100 % (0296) EtOAc/hexanes gradient over 10 min. The desired fractions were combined, concentrated and further dried under high vacuum O/N, yielding a white solid (2 g). LCMS (ESI+) m/z = 362,364 (M+l, M+3).

The chemical industry reduces the impact on the environment during synthesis 56621-89-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TEMPEST THERAPEUTICS, INC.; POWELL, David Andrew; ROPPE, Jeffrey Roger; SEIDERS, Thomas Jon; DING, Jinyue; SHENG, Tao; JACINTHO, Jason Duarte; (65 pag.)WO2019/79614; (2019); A1;,
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Reference of 37131-89-8, 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. 37131-89-8, name is 2,4-Dichloropyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

To a 50 ml three-necked flask was added successively the crude product (0.6 g, 3.1 mmol) in the previous step,Thionyl chloride (10 ml) and heated to 80 C for 4 hours.Concentrated to dryness under reduced pressure to give 0.6 g of 2,4-dichloro-5-pyrimidinecarboxylic acid chloride in a yield of 90%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,37131-89-8, 2,4-Dichloropyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SUZHOU WANGSHAN WANGSHUI BIOMEDICAL CO LTD; TOPHARMAN SHANGHAI CO LTD; SHANDONG TOPHARMAN PHARMACEUTICAL CO LTD; TIAN, GUANGHUI; LI, JUNQI; (17 pag.)CN104650045; (2017); B;,
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Synthetic Route of 144927-57-1, 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 144927-57-1, name is Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred mixture of ethyl 4-chloro-7H-pyrrolo[2,3-ii|pyrimidine-5-carboxylate (4.00 g, 17.7 mmol) and SEMC1 (4.71 mL, 26.6 mmol) in DMF (90 mL) was added sodium hydride (0.851 g, 21.3 mmol) portion-wise at 0 C. The resulting yellow suspension was stirred at 0 C for one hour and then allowed to warm to room temperature over one hour. The reaction was quenched with water slowly then extracted with ethyl acetate (x3). The combined organic layers were washed with brine (150 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with 0-50% ethyl acetate/hexane to afford ethyl-4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo [2,3 –Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
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Electric Literature of 13036-57-2 , The common heterocyclic compound, 13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, 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.

To a solution of ethyl 3-{[(2,6-diotafluorophenyl)sulfonyl]amiotano}-4-fluorobenzoate (5 0 g, 13 9 mmol) in THF (100 mL) was added 1 0 M LHMDS in THF (34 8 mL, 34 8 mmol) A solution of 2-chloro-4-methylpyriotamiotadiotane (2 7 g, 20 9 mmol) in THF (100 mL) was added dropwise over 30 mm, and the reaction was stirred overnight at rt The reaction was quenched with 10 mL of MeOH and concentrated, and the residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate The aqueous layer was extracted with 2×50 mL EtOAc, and the combined organic layers were passed through a pad of silica gel, concentrated, and adsorbed onto silica gel The crude product was purified via flash chromatography with 0-100% EtOAc/DCM to generate 3 07 g (50% yield) of the product of Step B as a white powder ES- LCMS m/z 443 (M+H)

The synthetic route of 13036-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
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Electric Literature of 761440-16-8, 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 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

4-(4-Amino-5-isopropoxy-2-methyl-phenyl)-piperidine-l-carboxylic acid tert-butyl ester (170 mg, 0.488 mmol) from the previous step, (2,5-Dichloro-pyrimidin-4-yl)-[2-(propane- 2-sulfonyl)-phenyl]-amine (Intermediate 2, 169 mg, 0.488 mmol, 1 equiv.), xantphos (28 mg, 0.049 mmol, 0.1 equiv.), palladium acetate (5.5 mg, 0.024 mmol, 0.05 equiv.), and Cs2CO3 (477 mg, 1.46 mmol, 3 equiv.) are dissolved in anhydrous THF (6 mL). N2 is bubbled through the reaction mixture for 5 minutes and then the reaction vessel is sealed and heated with microwave irradiation to 150 0C for 20 min. The reaction is filtered and the filtrate concentrated under vacuum. After concentration, the crude product is purified by silica gel chromatography (gradient from hexanes to 30% ethyl acetate in hexanes) to give 4-(4-{5-chloro-4-[2-(propane-2- sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-5-isopropoxy-2-methyl-phenyl)-piperidine-l- carboxylic acid tert-butyl ester as a yellow film: ESMS m/z 658.3 (M + H+). This product (105 mg, 0.160 mmol) is dissolved in CH2Cl2 (3 mL) and treated with TFA (3 mL). After 45 min., the reaction is concentrated under vacuum. 1 N HCl in Et2O (5 mL x 2) is added causing the product HCl salt to precipitate. The solvent is removed by decantation. The resulting 5- Chloro-N2-(2-isopropoxy-5-methyl-4-piperidin-4-yl-phenyl)-N4-[2-(propane-2-sulfonyl)- phenyl]-pyrimidine-2,4-diamine (66) is dried under high vacuum, generating an off-white powder: 1H NMR (400 MHz, DMSO-J6 + trace D2O) delta 8.32 (s, IH), 8.27 (d, IH), 7.88 (d, IH), 7.67 (dd, IH), 7.45 (dd, IH), 7.42 (s, IH), 6.79 (s, IH), 4.56-4.48 (m, IH), 3.49-3.32 (m, 3H), 3.10-2.91 (m, 3H), 2.09 (s, 3H), 1.89-1.77 (m, 4H), 1.22 (d, 6H), 1.13 (d, 6H); ESMS m/z 558.1 (M + H+).

According to the analysis of related databases, 761440-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; WO2008/73687; (2008); A2;,
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Pyrimidine – Wikipedia

Application of 33097-13-1 ,Some common heterocyclic compound, 33097-13-1, molecular formula is C6H3Cl2N3S, 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.

(S)-1-(1-Methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine 2,2,2-trifluoroacetate (1562 mg, 4.23 mmol) in THF (27.5 mL) along with 4,6- dichloro-2-(methylthio)pyrimidine-5-carbonitrile (931 mg, 4.23 mmol) and Et3N (1297 mu, 9.31 mmol) were added to a pear-shaped flask. The resulting mixture was stirred at room temperature for 2 hours and then concentrated to give the title compound, which was used in next step without further purification. ESI-MS m/z [M+H]+ calc’d for C20H19ClN8S, 439.11; found 439.4.

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. 33097-13-1, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHANG, Edcon; NOTZ, Wolfgang Reinhard Ludwig; WALLACE, Michael B.; WO2014/11568; (2014); A1;,
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Synthetic Route of 306960-77-0, 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. 306960-77-0, name is 2-(Trifluoromethyl)pyrimidine-5-carboxylic acid, molecular formula is C6H3F3N2O2, 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.

2-(Trifluoromethyl)pyrimidine-5-carboxylic acid (44.39 g, 231 .1 mmol),methoxymethanine hydrochloride (33.8 g, 346.6 mmol) and DIPEA (119.5 mL, 924.3 mmol) were combined in DCM (750 mL) then HATU (105.4 g, 277.3 mmol) was added and the mixture stirred at RT for 2 h. The reaction mixture was washed with water (3 x 300 mL), the organic phase collected, dried (over Mg504), filtered andconcentrated in vacuo to give a viscous yellow oil. The crude material was purified by dry flash chromatography (eluting with 0 – 40 % EtOAc in heptane) to give 54.2 g (95% yield) of the title compound as a free flowing pale yellow oil.1H NMR (500 MHz, Chloroform-d): 6 [ppm] 9.22 (5, 2H), 3.61 (5, 3H), 3.43 (5, 3H). LCMS (Analytical Method A) Rt = 1 .03 mm, MS (ESipos): m/z = 235.9 (M+H).

According to the analysis of related databases, 306960-77-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); 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 262353-35-5, name is 2-Iodo-4-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Iodo-4-methoxypyrimidine

1-(4-Methoxypyrimidin-2-yl)ethanone 2-Iodo-4-methyoxypyrimidine (Intermediate 74; 1.62 g, 6.84 mmol) was dissolved in dry THF (20 ml), cooled down to -10 C., i-PrMgCl (2 M in ether, 3.42 ml, 6.84 mmol) was added and the reaction mixture was stirred at 0 C. for 1 hour. N-Methoxy-N-methyl acetamide (776 mg, 7.52 mmol) was added; the mixture was slowly warmed up to room temperature over night. Water (10 ml) was added and the reaction mixture was extracted with DCM. The organic layer was dried over MgSO4, concentrated and purified by column chromatography (Hex/EtOAc, gradient) to give the desired product as a yellowish solid (470 mg). MS (ES) (M+H)+: 153 for C7H8N2O2; NMR (CDCl3): 2.77 (s, 3H), 4.10 (s, 3H), 6.89 (d, 1H), 8.62 (d, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 262353-35-5.

Reference:
Patent; ASTRAZENECA AB; US2008/312255; (2008); A1;,
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Pyrimidine – Wikipedia

Related Products of 89284-85-5, Adding some certain compound to certain chemical reactions, such as: 89284-85-5, name is Methyl 2,5,6-trichloropyrimidine-4-carboxylate,molecular formula is C6H3Cl3N2O2, 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 89284-85-5.

Furfurylamine (0.155 g, 1.60 mmol) was added to a stirred solution of 6- methoxycarbonyl-2,4,5-trichloropyrimidine (prepared as described in example 4) (0.193 g, 0.80 mmol) and triethylamine (0.24 ml, 1.7 mmol) in dichloromethane (3 ml). The solution was stirred at ambient temperature for 18 hours, and then added to a mixture of ethyl acetate and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an orange solid. This was purified by column chromatography on silica using ethyl acetate:hexane (1 :2) as eluent to provide 2,5-dichloro-4-(furan-2-ylmethylamino)-6-methoxycarbonylpyrimidine as a pale yellow solid (0.195 g, 81 %). Characterising data for this compound are as follows: m.p. 110- 112 0C; 1H nmr (400 MHz, CDCI3) deltaH 7.40 (1H, m), 6.35 (2H, m), 6.16 (1H, br s), 4.72 (2H, d), 3.98 (3H, s) ppm.

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. 89284-85-5, Methyl 2,5,6-trichloropyrimidine-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA LIMITED; WO2009/81112; (2009); A2;,
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Pyrimidine – Wikipedia

Reference of 335654-06-3, 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 335654-06-3 as follows.

2-chloro-7H-pyrrolo[2,3-T]pyrimidine (330 mg; 2.15 mmol) and JV-iodosuccinimide (580 mg; 2.58 mmol) are taken up in 3.3 mL DMF and stirred for 1 h at 200C. The reaction mixture is extracted with sodium thiosulphate solution and ethyl acetate. The combined organic phases are dried, the solvent is eliminated in vacuo and A.21 (EtaPLC- MS: tRet. = 1.60 min; MS(M+Eta)+ = 280; method FEC3) is obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,335654-06-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; BOEHMELT, Guido; KOFINK, Christiane; KUHN, Daniel; MCCONNELL, Darryl; STADTMUELLER, Heinz; WO2010/7116; (2010); A2;,
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