Category: pyrimidines

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.20781-06-0, name is 2,4-Diaminopyrimidine-5-carboxaldehyde, molecular formula is C5H6N4O, molecular weight is 138.1273, as common compound, the synthetic route is as follows.category: pyrimidines

EXAMPLE 1 2,7-Diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (Prepared by the method of U.S. Pat. No. 3,534,039). To a solution of sodium 2-ethoxyethoxide prepared from 0.14 g of sodium and 60 mL of 2-ethoxyethanol was added 2.07 g of 2,4-diamino-5-pyrimidinecarboxaldehyde and 2.79 g of 2,6-dichlorophenylacetonitrile. The mixture is heated at reflux for 4 hours, cooled, and the insoluble product washed with diethylether to give 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine, mp 325-332 C. (MS).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20781-06-0, 2,4-Diaminopyrimidine-5-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Blankley; Clifton John; Doherty; Annette Marian; Hamby; James Marino; Panek; Robert Lee; Schroeder; Mel Conrad; Showalter; Howard Daniel Hollis; Connolly; Cleo; US5733913; (1998); A;,
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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 2802-62-2, name is 4,6-Difluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4,6-Difluoropyrimidine

b) Preparation of 4-Fluoro-6-[(alpha,alpha,alpha-trifluoro-m-tolyl)oxy]pyrimidine A solution of m-trifluoromethylphenol (74.5 g, 0.46 mol) in tetrahydrofuran (300 mL) is added dropwise to a mixture of 4,6-difluoropyrimidine (53.8 g, 0.46 mol) and potassium carbonate (60 g, 0.43 mol) in tetrahydrofuran (700 mL). The reaction mixture is stirred at room temperature for 3 days and poured into water. The resultant aqueous mixture is washed with 2Nsodium hydroxide solution and extracted with ethyl acetate. The organic extract is dried over anhydrous magnesium sulfate and concentrated in vacuoto obtain a liquid. the liquid is vacuum distilled to give the title product as an oil (87.4 g, 74% yield).

With the rapid development of chemical substances, we look forward to future research findings about 2802-62-2.

Reference:
Patent; American Cyanamid Company; EP794177; (1997); A1;,
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Reference of 1753-48-6, 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.1753-48-6, name is 2-Aminopyrimidine-5-carbonitrile, molecular formula is C5H4N4, molecular weight is 120.1121, as common compound, the synthetic route is as follows.

Example B.5 2-Amino-N-hydroxy-pyrimidine-5-carboxamidine; A stirred mixture of commercially available 2-amino-5-cyano-pyrimidine [CAS-No. 1753-48-6] (1.39 g, 11.6 mmol), hydroxylamine hydrochloride (1.61 g, 23.2 mol) and potassium carbonate (4.8 g, 34.7 mol) in ethanol (57 ml) was heated under reflux conditions for 3h. The reaction mixture was evaporated and purified by column chromatography on silica gel (dichloromethane/MeOH 9:1) to yield the title compound (1.28g, 72%) as an off-white solid. MS (EI) 153.1 [(M)+]; mp 218 C.

Statistics shows that 1753-48-6 is playing an increasingly important role. we look forward to future research findings about 2-Aminopyrimidine-5-carbonitrile.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2007/72879; (2007); A1;,
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Pyrimidine – Wikipedia

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. 62459-02-3, name is 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione, the common compound, a new synthetic route is introduced below. Application In Synthesis of 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione

To a solution of DIEA (30.1 g, 233 mmol, 40.7 mL, 3.00 eq) in POCl 3 (330 g, 2.15 mol, 200 mL) was added 7-benzyl-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine-2,4-diol (20.0 g, 77.7 mmol, 1.00 eq). The reaction mixture was stirred at 110° C. for 5 hours. The reaction mixture was concentrated under vacuum. The residue was dissolved in DCM (400 mL) and poured into saturated NaHCO 3 (200 mL). The mixture was extracted with DCM (2 400 mL). The combined organic layers were washed with brine (100 mL), dried over Na 2SO 4 and concentrated under vacuum. The residue was purified by silica gel chromatography (diethyl ether_DCM=10:1 to 0:1) to give 7-benzyl-2,4-dichloro-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine (7.70 g, 26.2 mmol, 33.7% yield) as a brown oil. 1HNMR (300 MHz, chloroform-d) delta=7.43-7.28 (m, 5H), 3.73 (s, 2H), 3.66 (br s, 2H), 2.84 (br s, 4H)

The synthetic route of 62459-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mirati Therapeutics, Inc.; Array BioPharma Inc.; Blake, James F.; Burgess, Laurence E.; Chicarelli, Mark Joseph; Christensen, James Gail; Cook, Adam; Fell, Jay Bradford; Fischer, John P.; Marx, Matthew Arnold; Mejia, Macedonio J.; Savechenkov, Pavel; Vigers, Guy P.A.; Smith, Christopher Ronald; Rodriguez, Martha E.; US2019/144444; (2019); A1;,
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Reference of 31169-27-4, 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.31169-27-4, name is 7-Bromo-4-chlorothieno[3,2-d]pyrimidine, molecular formula is C6H2BrClN2S, molecular weight is 249.52, as common compound, the synthetic route is as follows.

EXAMPLE 10 7-Bromo-3,4-dihydrothieno[3,2-d]pyrimidin-4-thione (Compound 1e) A solution of 7-bromo-4-chlorothieno[3,2-d]pyrimidine (see below for preparation) (2.0 g), sodium hydrosulfide hydrate (0.66 g) and N-methylpyrrolidinone (10 ml) was heated at 102° C. for 1 hour. Water (500 ml) and ethyl acetate (500 ml) were added and stirred for 1hour. The layers were separated and the aqueous phase extracted with ethyl acetate (300 ml). The combined organic extracts were washed with brine (300 ml), dried (MgSO4), treated with activated charcoal, then filtered through a silica pad and the solvent removed to give the title product, m.p. 328° C.

The chemical industry reduces the impact on the environment during synthesis 31169-27-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Agrevo UK Limited; US6432964; (2002); B1;,
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Pyrimidine – Wikipedia

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. 1074-41-5, name is 6-Amino-2-(methylthio)pyrimidin-4-ol, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Amino-2-(methylthio)pyrimidin-4-ol

General procedure: A mixture of equimolar amounts of 6-amino-2-(methylthio)pyrimidin-4(3H)-one (1) (1 mmol), ethylcyanoacetateor meldrum?s acid (2 or 5) (1 mmol) and aldehyde(3 or 6) (1 mmol) was added to a vial containinga magnetic stirring bar and [DMBSI]HSO4 (0.18 mmol,0.06g) and heated at 80 C in an oil bath. Stirring at 80C was continued until disappearance of the startingmaterials. At this stage, due to the poor solubility in theionic liquid, the product appears as a precipitate. Thereaction mixture was cooled and washed with water toextract the ionic liquid. The solid obtained was recrystallizedfrom ethanol to furnish the desired pure product.The ionic liquid was recovered from the aqueous extractsby evaporation under reduced pressure, and reusedin the next run.

The synthetic route of 1074-41-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nia, Roghayeh Hossein; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Shirini, Farhad; Rassa, Mehdi; Acta Chimica Slovenica; vol. 60; 4; (2013); p. 889 – 895;,
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Electric Literature of 4994-86-9, 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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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.

Under Ar(g), to a mixture of pyrazin-2-amine (1) (209mg, 2.2mmol), 4- chloro-2-methylpyrimidine (2) (257mg, 2.0mmol), Cs2C03 (1.30g, 4.0mmol) was added degassed dry 1 ,4-dioxane (13mL). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt and concentrated in vacuo, CH2CI2 (15ml_) and H20 (15mL) were added. The organic phase was separated and the water layer was extracted with CH2CI2 (15ml_). The organic layers were combined and Pd- scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (184mg, 49%). (0590) LCMS (ES): Found 188.1 [M+Hf.

According to the analysis of related databases, 4994-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); 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. 6320-15-6, name is 4-Chloro-2,6-dimethoxypyrimidine, the common compound, a new synthetic route is introduced below. category: pyrimidines

Example 83Synthesis of 3-[6-{4-[2,6-dimethoxypyrimidin-4-yl]piperazin-l-yl}-5- phenyl-2-(trifluoromethyl)pyrimidin-4-yl]benzenesulfonamide.Step 1:Preparation of 2,4-dimethoxy-6-piperazin-l-ylpyrimidine.Piperazine (1.23g, 14.32mmol) was treated with 6-chloro-2,4- dimethoxy pyrimidine (0.5g, 2.86mmol) in acetonitrile (5mL) and stirred at room temperature for 6 hours. Subsequently the reaction mixture was poured onto ice-cold water (25mL) and extracted with ethyl acetate (25mL). The organic layer was washed with aqueous sodium bicarbonate solution and evaporated to furnish the required compound.

The synthetic route of 6320-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORCHID RESEARCH LABORATORIES LIMITED; WO2007/83182; (2007); A2;,
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Reference of 89466-39-7, 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.89466-39-7, name is 4-Chloro-6-methoxy-2-methylpyrimidine, molecular formula is C6H7ClN2O, molecular weight is 158.59, as common compound, the synthetic route is as follows.

General procedure: To a degassed solution of4,6-dichloropyrimidine (200 mg, 1.0 equiv) and arylboronic acid (1.0 equiv) in iPrOH (4 mL) in a 20 mLmicrowave vial was added an aqueous solution of 2M Na2CO3 (2.5 equiv) and Pd(PPh3)4 (5.0 mol%)under an argon atmosphere and the resulting heterogeneous solution was further degassed for 10 min. Thevial was sealed and placed in an oil bath at 83 oC and the reaction mixture was refluxed for 18 h, cooled,diluted with H2O (20 mL) and the whole was extracted with EtOAc (3 X 30 mL). The combined organicextract was washed with brine, dried (Na2SO4), and evaporated under reduced pressure give an oil whichwas purified by gradient column chromatography on silica gel using EtOAc/hexanes as eluent to affordcompounds 9a-j.

The chemical industry reduces the impact on the environment during synthesis 89466-39-7, I believe this compound will play a more active role in future production and life.

Reference:
Article; Gupta, Sahaj; Melanson, Jennifer A.; Selim Hossain; Vaillancourt, Louis; Tanoury, Gerald J.; Nugent, William A.; Snieckus, Victor; Heterocycles; vol. 96; 9; (2018); p. 1549 – 1569;,
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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. 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, 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. SDS of cas: 42754-96-1

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine 1a (120 mg, 0.63 mmol), 4-methoxybenzylamine 1b (87.1 mg, 0.63 mmol) and triethylamine (64.13 mg, 0.63 mmol) were dissolved in 2 mL of tetrahydrofuran, and the reaction solution was stirred at room temperature for 1 hour. The reaction was stopped, and the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with elution system A to obtain the title compound 1c (140 mg, yield: 76.1%). MS m/z (ESI): 290.2 [M+1]

With the rapid development of chemical substances, we look forward to future research findings about 42754-96-1.

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; ZHANG, Guobao; SHU, Chunfeng; HU, Qiyue; HE, Feng; TAO, Weikang; (59 pag.)EP3546457; (2019); A1;,
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