Pyrimidines

137281-39-1 , The common heterocyclic compound, 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, 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.

General procedure: To a suspension of compound 6 (0.033 mmol) in N,N-dimethylformamide (5 mL), corresponding amine (RNH2) (0.033 mmol) and DIPEA (0.1 mmol) were added at about 10 C under nitrogen atmosphere. To this, diethylphosphorocyanidate(0.04 mmol) was added slowly over a period of 15 min. The resultant solution was stirred for 3 h at about 10 C. The reaction was complete by TLC (TLC system: 10% methanol in chloroform). Reaction was slowly quenched using saturated sodium-bi-carbonate solution and the resulted solid was stirred for 30min. Solid was collected by filtration and the wet cake was washed with saturated sodium-bi-carbonate solution. Upon drying the wet cake for an hour under vacuum, it was further suspended in methanol and stirred for 30 min, filtered, collected and dried to get respective pure compounds.

According to the analysis of related databases, 137281-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Balaraman, Selvakumar; Nayak, Nagaraj; Subbiah, Madhuri; Elango, Kuppanagounder P.; Medicinal Chemistry Research; vol. 27; 11-12; (2018); p. 2538 – 2546;,
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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 591-55-9, name is 5-Aminopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 591-55-9

To a solution of (9S)-2-(2-(trifluoromethyl)pyridin-4-yl)-7,8,9,10-tetrahydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine (0.5 g, 1.561 mmol), triethylamine (0.653 mL, 4.68 mmol) in THF (10 mL) was added bis(trichloromethyl) carbonate (0.232 g, 0.780 mmol) at 25 C. under nitrogen atmosphere and stirred at RT for 30 min. Then pyrimidin-5-amine (0.445 g, 4.68 mmol) was added and heated the reaction mixture at 65 C. for 16 h. Allowed to cool to RT and solvent was removed on rota-vapour, the crude was diluted with CH2Cl2 (20 ml) and washed with water (5 ml), brine solution (5 ml) followed by dried over sodium sulfate. The organic solvent was evaporated under reduced pressure to obtain the crude product. The crude mixture was purified by prep-HPLC (formic acid, ACN 25%) to afford (9S)-N-(pyrimidin-5-yl)-2-(2-(trifluoromethyl)pyridin-4-yl)-8,9-dihydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine-10(7H)-carboxamide (250 mg, 0.56 mmol, 45% yield) as an off white solid (TLC: 80% EtOAc in Hexane, Rf: 0.5), LCMS (m/z): 442.3 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 13.07 (s, 1H), 9.08-8.72 (m, 4H), 8.38 (dd, J=1.7, 0.9 Hz, 1H), 8.28 (dd, J=5.2, 1.6 Hz, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.79 (d, J=8.0 Hz, 1H), 4.85 (t, J=2.7 Hz, 1H), 3.43 (dd, J=13.7, 1.9 Hz, 1H), 3.33 (d, J=10.1 Hz, 2H), 2.91 (d, J=13.7 Hz, 1H), 2.15-1.79 (m, 2H), 1.33 (s, 2H).

Statistics shows that 591-55-9 is playing an increasingly important role. we look forward to future research findings about 5-Aminopyrimidine.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); 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. 1004-40-6, name is 6-Amino-4-hydroxy-2-mercaptopyrimidine. A new synthetic method of this compound is introduced below., 1004-40-6

General procedure: A mixture of freshly calcined K2CO3 (7.4 mmol), 2-thiouracil 2a-c (7.0 mmol), 2-(bromomethyl)-2-isoindole-1,3-dione (7.7 mmol), and anhydrous DMF (20 ml) was stirred at room temperature for 72 h. The reaction mixture was filtered, and the filtrate was evaporated to dryness. The obtained residue was taken up in 1 aqueous solution, the mixture was filtered, the filtrate was extracted with EtOAc (3¡Á50 ml), dried over MgSO4, filtered, and evaporated at reduced pressure. The solids collected by filtration were air-dried until constant mass, combined with the evaporated organic extract, and the obtained mixture was purified by preparative HPLC.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1004-40-6, 6-Amino-4-hydroxy-2-mercaptopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Novakov, Ivan A.; Sheikin, Dmitry S.; Chapurkin, Viktor V.; Nawrozkij, Maksim B.; Babushkin, Alexande S.; Kuznetsov, Yaroslav P.; Ruchko, Evsey A.; Kachala, Vadim V.; Maryshev, Anton Yu.; Schols, Dominique; Chemistry of Heterocyclic Compounds; vol. 56; 1; (2020); p. 67 – 72; Khim. Geterotsikl. Soedin.; vol. 56; 1; (2020); p. 67 – 72,6;,
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1500-85-2, 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. 1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, 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.

7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.4 g, 3.0 mmol) was dissolved in 10 mL DMF.NIS (0.74 g, 3.3 mmol) was added in portions under ice bath.After the feeding is completed, the ice bath is removed.The reaction was allowed to proceed at room temperature for 3 hours, and the reaction was confirmed to be complete by TLC. 20 mL of water was added to the reaction solution.It was extracted with ethyl acetate (30 mL*3), and the organic phase was washed with 20 mL of brine.Dry over anhydrous sodium sulfate, concentrate,The residue was separated into a pale yellow solid (0.56 g).The yield was 73%.

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. 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Xing Qingfeng; (59 pag.)CN110194772; (2019); A;,
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504-17-6, 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. 504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, 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.

General procedure: A mixture of an aldehyde (0.25 mmol), 2-thiobarbituric acid (0.5 mmol), ammonium acetate (0.3 mmol), and CuFe2O4 (10 mol%), with distilled H2O, in an open tall beaker was irradiated inside microwave oven at 100 W for an appropriate time (monitored by TLC). After completion of the reaction, for removing the catalyst, the hot solution was filtrated with external magnetic for several times. The solvent was evaporated, and the precipitate was washed from ethanol and hot water to afford the pure product.

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. 504-17-6, 4,6-Dihydroxy-2-mercaptopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Naeimi, Hossein; Didar, Asieh; Rashid, Zahra; Journal of the Iranian Chemical Society; vol. 14; 2; (2017); p. 377 – 385;,
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1193-24-4, 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. 1193-24-4, name is 4,6-Dihydroxypyrimidine. A new synthetic method of this compound is introduced below.

EXAMPLES 1-6 General Procedure for Conversion of 4,6-dihydroxypyrimidine (DHP) to 4,6-dichloropyrimidine (DCP): The reaction vessel is a Morton-type flask fitted with a heating mantle, a mechanical agitator, a temperature probe, a phosgene dip pipe (which also serves as a nitrogen inlet when phosgene is not being introduced to the reactor), and a dry ice condenser. The dry ice condenser is vented into a caustic scrubber. The reactor is charged with 4,6-dihydroxypyrimidine, solvent, and catalyst, forming a slurry. The agitator is started and the mixture is heated to 105-110 C. When this temperature range is reached, phosgene gas is introduced subsurface to the reaction mixture via the dip pipe. Phosgene addition is continued over 3-5 hours. During the addition, phosgene escaping the reaction is condensed by the dry ice condenser and returned to the reactor. This reflux of phosgene begins shortly after the phosgene addition is begun, and continues throughout the course of the reaction.

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. 1193-24-4, 4,6-Dihydroxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Doyle, Timothy John; Wehrenberg, Peter Karl; Standen, Michael Charles Henry; US2002/42514; (2002); A1;,
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137281-39-1, 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 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. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a suspension of compound 6 (0.033 mmol) in N,N-dimethylformamide (5 mL), corresponding amine (RNH2) (0.033 mmol) and DIPEA (0.1 mmol) were added at about 10 C under nitrogen atmosphere. To this, diethylphosphorocyanidate(0.04 mmol) was added slowly over a period of 15 min. The resultant solution was stirred for 3 h at about 10 C. The reaction was complete by TLC (TLC system: 10% methanol in chloroform). Reaction was slowly quenched using saturated sodium-bi-carbonate solution and the resulted solid was stirred for 30min. Solid was collected by filtration and the wet cake was washed with saturated sodium-bi-carbonate solution. Upon drying the wet cake for an hour under vacuum, it was further suspended in methanol and stirred for 30 min, filtered, collected and dried to get respective pure compounds.

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 137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid.

Reference:
Article; Balaraman, Selvakumar; Nayak, Nagaraj; Subbiah, Madhuri; Elango, Kuppanagounder P.; Medicinal Chemistry Research; vol. 27; 11-12; (2018); p. 2538 – 2546;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

90213-66-4, 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. 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below.

A stirred solution of S-1 (2.00 g, 10.7 mmol) in CH2Cl2(20 mL) taken in a round- bottom flask was charged with DIPEA (3.7 mL, 21.4 mmol), DMAP (0.039 g, 0.32 mmol) and p-toluene sulfonyl chloride (2.25 g, 11.7 mmol) successively at ambient temperature under nitrogen atmosphere. The reaction mixture was stirred for 2 h at same temperature. The reaction mixture was diluted with CH2Cl2(100 mL) and was washed with water (40 mL) and HCl (1 N, 40 mL). The combined organic layer was washed with brine (1 ¡Á 50 mL), dried over anhydrous Na2SO4and was concentrated under reduced pressure. The obtained residue was washed with hexanes (2 ¡Á 50 mL) and was dried under vacuum to afford S-2 (3.50 g, 95%, AMRI lot IN-SKY-C-03) as an off-white solid. The compound was characterized by1H NMR analysis.1H NMR (400 MHz, CDCl3): delta 8.03 (d, J = 8.4 Hz, 2H), 7.68 (d, J = 4 Hz, 1H), 7.29 (d, J = 8.12 Hz, 2H), 6.60 (d, J = 4 Hz, 1H), 2.36 (s, 3H).

Statistics shows that 90213-66-4 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; SOUTHERN RESEARCH INSTITUTE; AUGELLI-SZAFRAN, Corinne, E.; SUTO, Mark; GALEMMO, Robert; MOUKHA-CHAFIQ, Omar; GUPTA, Vandana; ANANTHAN, Subramaniam; (254 pag.)WO2017/106771; (2017); A1;,
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1820-81-1, 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. 1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, 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.

Example 1; compound 1 A 50OmL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 1100C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10% EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69%).; Example 3; compound 78NMM, THF -780CA 500-mL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 110 0C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10% EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69%).; Example 4 compound 80A 500-mL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 110 0C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10% EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69%).; Example 5 compound 84a bA 50OmL round bottomed flask was charged with 5-chlorouracil a (25.0 g, 170 mmol, 1.0 equiv) and phosphoryl chloride (159 mL, 1.7 mol, 10 equiv). The reaction vessel was equipped with a vigoreaux column followed by careful addition of diisopropylethylamine (59 mL, 340 mmol, 2.0 equiv) over 1 minute. Evolution of white fumes was observed during the addition of diisopropylethylamine. The reaction was then heated to 1100C and stirred for 3 h. The reaction was cooled to ambient temperature and concentrated in vacuo to crude brown oil. The residual oil was quenched by careful addition of ice chips followed by cold water (100 mL). The aqueous mixture was extracted with diethyl ether and the organic layer washed with brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield crude yellow oil. The crude oil was purified by silica gel chromatography, 0-10% EtOAc/hexane, to provide 2,4,5-trichloropyrimidine b as colorless oil (21.4 g, 69%).

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. 1820-81-1, 5-Chlorouracil, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; WO2008/79719; (2008); A1;,
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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 36315-01-2 as follows., 36315-01-2

EXAMPLE 1 N-(2-Chloroimidazo[1,2-a]pyridine-3-ylsulfonyl)-N’-(4,6-dimethoxy-2-pyrimidinyl)urea (Compound No. 1) STR55 In 30 ml of acetonitrile are dissolved 2.32 g (0.01 mole) of 2-chloroimidazo[1,2-a]pyridine-3-sulfonamide and 2.02 g (0.02 mole) of triethylamine, followed by addition of 1.60 g (0.01 mole) of phenyl chloroformate with stirring at 10 to 20 C. The mixture is further stirred at 20 to 25 C. for 30 minutes, and to the mixture are added 1.00 g (0.010 mole) of methanesulfonic acid and then 1.55 g (0.01 mole) of 2-amino-4,6-dimethoxypyrimidine. The mixture is stirred at 60 C. for 15 minutes. After cooling, the crystals which separates out are collected by filtration and washed with water 3 times with 10 ml of water each. The crystals were then dried in vacuo over P2 O5 to give 3.42 g (yield 83.0%) of the title compound. m.p. 183-184 C. (decomp.). NMR (DMSO-d6) delta: 3.95 (s, 6H), 6.0 (s, 1H), 7.3-7.5 (m, 1H), 7.5-7.9 (m, 2H), 8.97 (d, 1H), 10.65 (s, 1H), 12.8 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 36315-01-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4994571; (1991); A;,
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