Category: pyrimidines

Synthetic Route of 51421-99-9 , The common heterocyclic compound, 51421-99-9, name is 4-Chloro-2-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

159.2 2-Chloro-5-(2-methoxyDyrimidine-4-carbonyl)benzoic acid methyl esterA 60% suspension of NaH in mineral oil (51 mg) was added to a solution of 4-chloro-2- methoxypyrimidine (123 mg), intermediate 159.1 (170 mg) and dimethylimidazolium iodide (96 mg) in dioxane (35 mL). The reaction mixture was heated to reflux for 4h30 and ON at RT. It was diluted with water and extracted with EtOAc. The organic phase was dried over MgS04 and concentrated in vacuo. The crude was purified by CC (Hept/EtOAc 1/0 to 7/3) to give 49 mg of the titled compound as a light yellow solid.LC-MS (B): tR = 0.77 min; [M+H]+: 307.19

The synthetic route of 51421-99-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; WO2012/114268; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
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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.14080-23-0, name is 2-Cyanopyrimidine, molecular formula is C5H3N3, molecular weight is 105.0974, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Cyanopyrimidine

To a stirring solution of 2-cyanopyrimidine (2.0 g, 19.0 mmol) in methanol (50 mL) were added 10%Pd/C (300 mg), 12 N HCI (1.5 mL) under 2 atmosphere. The reaction mixture was stirred under atmosphere (balloon pressure) at RT for 3 h. After consumption of the starting material (by TLC), the reaction mixture was filtered through a pad of celite and the pad was washed with methanol. Obtained filtrate was concentrated under reduced pressure to afford crude compound which was triturated with diethyl ether to obtained compound 2S-Y (1.2 g, 44%) as white solid. 1H-NMR: (500 MHz, DMSO-i): delta 8.87 (d, J= 5.0 Hz, 2H), 8.69 (br s, 2H), 7.52 (t, J= 5.0 Hz, 1H), 4.24 (s, 2H); Mass (ESI): 1 10.3 [M++l]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14080-23-0, 2-Cyanopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NAUREX, INC.; LOWE, John, A., III; KHAN, M., Amin; WO2014/120783; (2014); A1;,
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Pyrimidine – Wikipedia

Application of 56844-12-3 , The common heterocyclic compound, 56844-12-3, name is 6-Bromo-4-chlorothieno[2,3-d]pyrimidine, molecular formula is C6H2BrClN2S, 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.

A stirred solution of 6-bromo-4-chlorothieno[2,3-d]pyrimidine (4.0g, 0.016mol) in anhydrous tetrahydrofuran (100ml) was cooled in a dry-ice/acetone bath and treated, under a nitrogen atmosphere, with lithium diisopropylamide (1.8M solution in tetrahydrofuran, 9.0ml, 0.016mol) over about 20 minutes. The resultant dark solution was stirred in the cold for 1 hour and then treated with a mixture of water (5ml) and tetrahydrofuran (20ml) over about 20 minutes. The mixture was then allowed to warm up to about 0C before being poured into water (250ml) and extracted with dichloromethane (SxlOOml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude product. Purification by flashchromatography (silica) eluting with dichloromethane gave 5-bromo-4-chlorothieno[2,3-cQpyrimidine as a pale brown solid (3.8g).

The synthetic route of 56844-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENTION DISCOVERY LIMITED; WO2004/111057; (2004); A1;,
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Application of 108381-28-8, 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. 108381-28-8, name is 4-(Benzyloxy)-2-chloropyrimidine, molecular formula is C11H9ClN2O, 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.

Step 1-Synthesis of 4-(benzyloxy)-N-(4-(4′-morpholino-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrano[2,3-d]pyrimidine]-2′-yl)phenyl)pyrimidin-2-amine (cq): 4-(4′-morpholino-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrano[2,3-d]pyrimidine]-2′-yl)aniline (co) (79.5 mg, 0.235 mmol), 4-(benzyloxy)-2-chloropyrimidine (63.4 mg, 0.287 mmol), bis(dibenzylideneacetone)palladium(0) (8.2 mg, 0.014 mmol), sodium tert-butoxide (35.8 mg, 0.372 mmol), and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (9.8 mg, 0.025 mmol) were weighed into a microwave vial. The vial was evacuated and purged 3× with N2, then degassed toluene (2.1 mL, 2.0E1 mmol) was added and the vial sealed. The reaction was microwaved at 120 C. for 20 min. The reaction mixture was filtered through Celite, washing extensively with CH2Cl2. This was then concentrated onto silica gel and subjected to column chromatography using a 12 g column, with a gradient of 0% to 100% ethyl acetate in hexanes. The product containing fractions were combined and evaporated under reduced pressure to give 4-(benzyloxy)-N-(4-(4′-morpholino-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrano[2,3-d]pyrimidine]-2′-yl)phenyl)pyrimidin-2-amine: 1H NMR (400 MHz, DMSO) delta 8.75 (s, 1H), 8.12 (d, J=8.7 Hz, 2H), 7.45 (d, J=8.8 Hz, 2H), 6.98 (d, J=6.5 Hz, 1H), 4.81-4.67 (m, 3H), 4.44 (t, J=5.7 Hz, 2H), 3.79-3.69 (m, 4H), 3.48-3.40 (m, 4H), 2.71 (t, J=5.9 Hz, 2H), 1.86 (t, J=5.9 Hz, 2H), 1.01 (t, J=6.0 Hz, 2H), 0.73 (t, J=6.3 Hz, 2H).

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 108381-28-8, 4-(Benzyloxy)-2-chloropyrimidine.

Reference:
Patent; Genentech, Inc.; US2010/331305; (2010); A1;,
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Pyrimidine – Wikipedia

Application of 50270-27-4, 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. 50270-27-4, name is 2,4,6-Trichloropyrimidine-5-carbaldehyde, molecular formula is C5HCl3N2O, 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.

To 2,4,6-trichloropyrimidine-5-carbaldehyde (0.693 g, 3.27 mmol) in EtOH (10 mL) at -78 °C under argon was added (tetrahydro-2H-pyran-4- yl)hydrazine hydrochloride (0.5 g, 3.27 mmol) followed by dropwise addition of TEA (2.05 mL, 14.7 mmol). The mixture was stirred at -78 °C for 1 h, then at 0 °C for 2 h. The mixture was then concentrated under reduced pressure onto Celite and purified by silica gel chromatography eluting with DCM to afford 4,6-dichloro-l-(tetrahydro-2H- pyran-4-yl)-lH-pyrazolo[3,4-d]pyrimidine (440 mg, 49percent). LCMS (ESI) m/z 273 (M + H)+.

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 50270-27-4, 2,4,6-Trichloropyrimidine-5-carbaldehyde.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; WO2012/30924; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Adding a certain compound to certain chemical reactions, such as: 28485-17-8, 5-Carbethoxyuracil, 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, Formula: C7H8N2O4, blongs to pyrimidines compound. Formula: C7H8N2O4

Step i. Ethyl 2,4-dichloropyrimidine-5-carboxylate Under an N2 atmosphere, a mixture of 5-carbethoxyuracil (1.0 g, 5.4 mmol) and POCl3 (10 mL) was heated at reflux for 30 minutes. The solution was concentrated under reduced pressure to remove the excess of POCl3, and the residue was poured into ice (20 g). CH2Cl2 (100 mL) was added, and the mixture was basified to pH 9 using saturated aqueous NaHCO3 solution. The organic portion was dried over MgSO4 and concentrated to obtain ethyl 2,4-dichloropyrimidine-5-carboxylate as a yellow oil (900 mg, 75%).

The synthetic route of 28485-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Martinborough, Esther; Zimmermann, Nicole; Perni, Robert B.; Arnost, Michael; Bandarage, Upul K.; Maltais, Francois; Bemis, Guy; US2006/160817; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 109-12-6, Pyrimidin-2-amine, 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, 109-12-6, blongs to pyrimidines compound. Product Details of 109-12-6

General procedure: 0.5 mol% ruthenium(II) catalyst was stirred with 4 mmol ofKOH in toluene. To this mixture, 2 mmol of alcohol and 2 mmolof amine were added and the temperature was raised up to120 C. The progress of the reactions was monitored using TLC.As soon as the reaction was completed, the mixture was cooledto room temperature and added 3 mL of distilled water. The combinedmixture was extracted with CH2Cl2 and dried by addingmagnesium sulfate. The crude product was purified by columnchromatography (n-hexane/EtOAc) and characterized by 1H NMRspectral analyses. The 1H NMR data obtained for the catalytic productswere compared with literature [19].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109-12-6, its application will become more common.

Reference:
Article; Prakash, Govindan; Ramachandran, Rangasamy; Nirmala, Muthukumaran; Viswanathamurthi, Periasamy; Sanmartin, Jesus; Inorganica Chimica Acta; vol. 427; (2015); p. 203 – 210;,
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Related Products of 13036-57-2 ,Some common heterocyclic compound, 13036-57-2, 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 20L reaction bottle into the 100g/3L of the potassium hydroxide aqueous solution, then adding 250g of compound B, 650g potassium permanganate of hot water after dissolving dropping to the bottle, about water 15L. Temperature control is dropped in the 5 – 15 C, after the clip 20 C reaction 24h, TLC monitoring (raw material reaction not end). After the reaction is added to the reactant 120g of sodium bisulfite, stirring 15min, reaction fluid settlement for a period of time is colorless, if they are not re-added sodium bisulfite. Adding 4L dichloromethane extraction 3 time separation and recovery of the unreacted raw materials (for recovering raw material 40g). Then added to the aqueous phase in the diatomaceous earth filter, the filtrate concentrated hydrochloric acid to adjust the pH=2 – 3, the stirring 30min, concentrated to dry.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13036-57-2, its application will become more common.

Reference:
Patent; Anhui CCID Biotechnology Co., Ltd.; Wei, Xiaoyan; He, Ying; Wei, Wei; Yu, Lideng; (6 pag.)CN106083734; (2016); A;,
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Synthetic Route of 582313-57-3, Adding some certain compound to certain chemical reactions, such as: 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H3ClFN3, 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 582313-57-3.

To containCCl4 (5 mL, 51 mmol)Add hexamethylphosphoramide to a solution of 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose (9.13 g, 30 mmol) in toluene (100 mL) 7.2 mL, 40 mmol). After stirring at 0 C for 2.5 hours,The reaction mixture was added to 4-chloro-5-fluoro-7H-pyrrole [2,3-d]pyrimidine (14-1, 3.1 g,20 mmol), a solution of tris(3,6-dioxaheptyl)amine (TDA-1) (3 mL, 9 mmol) and KOH (2.6 g, 4.5 mmol) in toluene (100 mL)The entire reaction mixture was stirred at room temperature for 24 hours.The reaction was terminated by the addition of a saturated aqueous solution of NH 4 Cl.Transfer the entire mixture to a separatory funnel. The aqueous layer is extracted with AcOEt.The combined organic layers were washed with brine.Dry (Na2SO4)Concentration in vacuo gave the crude product 17-2.

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. 582313-57-3, 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Hongyi Biological Technology Co., Ltd.; Wu Rongguang; Yi Dewu; (140 pag.)CN109694397; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3764-01-0, 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 3764-01-0, name is 2,4,6-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1 : Synthesis of 2-[2-(pyridin-2-yl)-ethoxy]-4-[N’-(3-methyl-benzilidene)- hydrazino]-6-(morpholin-4-yl)-pyrimidine (Compound 6) EPO Step 1.A 2-liter, 3-neck flask equipped with mechanical stirrer, thermometer and dropping funnel was loaded with ethanol (375 mL), water (375 mL) and morpholine, (1.01 mol, 88 g); the resulting solution was cooled (with sodium chloride- ice mixture) to about 0 0C and a solution of 2,4,6-trichloropyrimidine (91.17 g, 0.5 mol) in ethyl acetate (37.5 mL) was added dropwise in about 20 minutes, to maintain temperature below 10 0C. The dropping funnel was rinsed twice with ethyl acetate (3 mL), and the rinses were transferred to the reaction mixture. The reaction was checked by TLC to determine when the reaction was complete. After completion of the reaction, ice water (375 mL) was added, and reaction was allowed to stir for 30 minutes to complete precipitation. The colorless solid was filtered out, washed 6 times with water (225 mL per wash) and vacuum-dried at 40-50 0C until a constant weight of the product was maintained. The product (114.7 g, 98% yield) was a mixture of regioisomers 2,4-dichloro-6-(morpholin-4-yl)-pyrimidine and 4,6-dichloro-2- (morpholin-4-yl)-pyrimidine in about a 3.9: 1 ratio (Product 1).

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/53112; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia