Pyrimidines

Application of 1431412-19-9, 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. 1431412-19-9, name is 4-Methoxyfuro[3,2-d]pyrimidine-6-carboxylic acid. A new synthetic method of this compound is introduced below.

To a solution of the above 4-methoxyfuro[3,2-d]pyrimidine-6-carboxylic acid (83; 3 g, 15 mmol), benzyltriethyl ammonium chloride (7 g, 31 mmol) and dimethyl aniline (3 mL, 24 mmol) in acetonitrile (70 mL) at 60 C was added phosphorous oxychioride (10 mL). The mixture was stirred at 60 C for 4 h. The reaction mixture was concentrated in vacuo, the residue was dissolved in THF, and ammonium hydroxide solution was added until pH = 9. The solid was filtered and dried to obtain 4-chlorofuro[3,2-d]pyrimidine-6-carboxamide(Compound 84; 1.0 g, 33%). MS (ESI) calcd for C7H4C1N302: 197.00; found: 198 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1431412-19-9, 4-Methoxyfuro[3,2-d]pyrimidine-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; BLUM, Charles, A.; DISCH, Jeremy, S.; EVINDAR, Ghotas; PERNI, Robert, B.; WO2014/138562; (2014); A1;,
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Electric Literature of 56-06-4, 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 56-06-4, name is 2,6-Diaminopyrimidin-4(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

174 mg of sodium hydride (60% in mineral oil, 4.36 mmol) are added in portions under an argon atmosphere to a vigorously stirred solution of 500 mg (3.96 mmol) of 2,6-diaminopyrimidin-4-ol in 10 ml of DMF. After 30 min, 700 mul (5.15 mmol) of ethyl trifluoromethanesulfonate are added dropwise, and the solution is stirred for a further 20 min. Methanol (1 ml) is then added to the reaction mixture, which is directly purified by preparative HPLC. Combining the product fractions and removing the solvent result in 370 mg (64% of theory) of the title compound as a white solid. LC-MS (method 5): Rt=2.24 min; MS (ESIpos): m/z=155 [M+H]+ 1H-NMR (400 MHz, DMSO-d6): delta=1.21 (t, 3H), 4.12 (q, 2H), 5.00 (s, 1H), 5.87 (s, 2H), 6.01 (s, 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 56-06-4, 2,6-Diaminopyrimidin-4(1H)-one.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/35902; (2010); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 252723-16-3, Adding some certain compound to certain chemical reactions, such as: 252723-16-3, name is 7-Benzenesulfonyl-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C13H10ClN3O2S, 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 252723-16-3.

Step 3To the solution of 4-chloro-6-methyl-7-(phenylsuIfonyl)-7H-pyrrolo[‘2,3-d]pyrimidine(10 g, 32.5. mmol, 1.0 eq) in THF (400 mL), t-BuOK (18.23 g, 163.0 mmol, 5 eq) was added and stirred at RT for 12 h. Sat, NaHC03 (50 mL) was added and extracted with EtOAc. The organic layers were separated, dried and concentrated to afford 4-chloro-6-methyl-7H- pyrrolo[2,3-d]pyrimidine as a brown solid (2.7 g, 50 % in yield).

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. 252723-16-3, 7-Benzenesulfonyl-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; WO2012/158764; (2012); A1;,
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Synthetic Route of 2244-11-3, 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 2244-11-3, name is Pyrimidine-2,4,5,6(1H,3H)-tetraone hydrate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 0.5 mmol of alloxan monohydrate (0.08 g) and suitable methyl ketone were suspended in 5 mL of glacial acetic acid and reacted in a Syncore apparatus set at the temperature of 115 C, shaking at 120 rpm and reaction time 3 h. All the targeted compounds precipitated after cooling and were recrystallized from ethanol. Compounds 19 and 20 were obtained as a mixture in a 36:64 ratio (total yield 75%); chromatographic purification of the crude (gradient eluent: methanol in dichloromethane 0-10%) afforded the pure final compounds.5.1.2.12 5-[3-(Biphen-4-yl)-2-oxopropyl]-5-hydroxy-hexahydropyrimidine-2,4,6-trione (19) 27% Yield, mp 173-5 C (decomp. 150 C). 1H NMR (acetone-d6) delta 10.24 (s, 2H, NH), 7.60-7.67 (m, 2H), 7.43-7.54 (m, 3H), 7.30-7.37 (m, 3H), 7.16-7.19 (m, 1H), 5.80 (s, 1H, OH), 3.30 (s, 2H), 2.14 (s, 2H). Anal. % (C19H16N2O5) calculated: C 64.77, H 4.58, N 7.95; found C 64.47, H 4.27, N 7.67.

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 2244-11-3, Pyrimidine-2,4,5,6(1H,3H)-tetraone hydrate.

Reference:
Article; Nicolotti, Orazio; Catto, Marco; Giangreco, Ilenia; Barletta, Maria; Leonetti, Francesco; Stefanachi, Angela; Pisani, Leonardo; Cellamare, Saverio; Tortorella, Paolo; Loiodice, Fulvio; Carotti, Angelo; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 368 – 376;,
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Pyrimidine – Wikipedia

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. 32779-37-6, name is 2,5-Dibromopyrimidine, molecular formula is C4H2Br2N2, 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. category: pyrimidines

To a stirred solution of 2,5 dibromo pyrimidine (0.32 g, 1.332 mmol), obtained from Preparation 44, in toluene (6 imL) was added 6-(tert-butyl-dimethyl-silanyloxy)-naphthalen-2-yl-boronic acid (0.48 g, 1.585 mmol), EtOH (2 ml_), water (1 ml_) and Na2CO3 (0.35 g, 3.33 mmol). Argon was bubbled through the reaction mixture for 30 minutes. Then Pd(PPh3)4 (0.075 g, 0.065 mmol) was added and the mixture was heated in a sealed tube at 90 0C for 16 hours. The solvent was evaporated under vacuum and the reaction mixture was diluted with ethyl acetate (15 ml_). The ethyl acetate layer was filtered through celite then washed with water (10 ml_) and brine (10 ml_). It was then dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silica gel by using ethyl acetate : hexane (1 :9) mixture to give the title compound as a white solid (546 mg).1H NMR (400 MHz, CDCI3): delta= 8.86 (s, 1 H), 8.83 (s, 1 H), 8.40 (d, 1 H), 7.87 (d, 1 H), 7.76 (d, 1 H), 7.31 (s, 1 H), 7.20 (s, 1 H), 7.10 (dd, 1 H), 1.02 (s, 9H), 0.26 (s, 6H). LCMS (System 1 ) (run time = 5 min): Rt = 3.57 min; m/z 415; 417 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 32779-37-6.

Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; PRYDE, David Cameron; TRAN, Thien Duc; WO2011/4276; (2011); A1;,
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Synthetic Route of 4212-49-1 ,Some common heterocyclic compound, 4212-49-1, molecular formula is C6H8N2O2, 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.

N, N-DIISOPROPYLETHYLAMINE (195 mL, 0.86 mol) (Aldrich) was added slowly to a mixture of 5-ethyl uracil (52.3 g, 0.37 mol) (from Example LC, suprn) and phosphorous oxychloride (150 mL, 1.61 mol) (Aldrich) with external cooling in a cold water bath. The mixture was heated at reflux for 3.8 hours and cooled to room temperature. Mixture was then poured into ice (300 g). Ethyl acetate (100 mL) was added and mixture stirred at 20 C for 30 minutes with cooling in an ice-water bath. The resulting mixture was filtered through CELITEE and the filtrate extracted with ethyl acetate-hexanes (1: 1,3 X 300 mL). The combined organic layers was washed with water (250 mL), dried over sodium sulfate, filtered and concentrated to dryness. This residue was dissolved in ethyl acetate- hexanes (1 : 1) and filtered through TLC grade silica gel and eluting with the same solvent. The filtrate was concentrated to dryness to give 2,4-dichloro-5-ethyl-pyrimidine. (Yield 56.3 g, 85.2%).

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. 4212-49-1, 5-Ethyluracil, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/41821; (2004); A1;,
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Pyrimidine – Wikipedia

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. 32779-37-6, name is 2,5-Dibromopyrimidine, molecular formula is C4H2Br2N2, 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. Formula: C4H2Br2N2

Example 73(S)-4-(4-(5-(2,2,2-Trifluoroethoxy)pyrimidin-2-ylamino)phenethyl)-4,5-dihydrooxazol-2-aminea) 5-Bromo-2-(2,2,2-trifluoro-ethoxy)-pyrimidineTo sodium hydride (303 mg) under an argon atmosphere at 0 C. was added dropwise 2,2,2-trifluoroethanol (775 mul) and the mixture was then stirred at RT for 90 min. A solution of 2,5-dibromopyrimidine (1.5 g) in DMF (8 ml) was then added and stirring continued at RT for 2 hours. The reaction mixture was poured into ice (50 mL) and extracted with EtOAc (2×50 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to afford 5-bromo-2-(2,2,2-trifluoro-ethoxy)-pyrimidine (790 mg, 49%) as a yellow oil which was used in the next step without further purification. MS (EI): 258 ([{81Br}M]+), 256 ([{79Br}M]+), 189 ([{81Br}M-CF3]+), 187 ([{79Br}M-CF3]+).

With the rapid development of chemical substances, we look forward to future research findings about 32779-37-6.

Reference:
Patent; Nettekoven, Matthias; Norcross, Roger; Polara, Alessandra; US2012/108609; (2012); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 49844-90-8, 4-Chloro-2-(methylthio)pyrimidine, 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, 49844-90-8, blongs to pyrimidines compound. Recommanded Product: 49844-90-8

Bromo trimethylsilane (23 mL, 174.31 mmol) was addedto a solution of 4-chloro-2-methylsulfanylpyrimidine (2.9 g 25 mmol) inacetonitrile (240 mL).The mixture was stirred for 30 h at 40C. The reactionwas monitored by TLC. After cooling to room temperature, NaHCO3saturated solution (250 mL) was added and the product was extracted with AcOEt.The organic layer was dried over Na2SO4, filtered, andevaporated under reduced pressure. The crude residue was purified bychromatography on silica gel using dichloromethane-ethyl acetate (9:1).Evaporation of the eluent in vacuum gave the desired compound in 96% yield(4.66 g) as colorless oil. Litt 1H NMR (CDCl3): delta 2.56(s, 3H, SCH3), 7.16 (d,1H, J = 5.2 Hz, H-5pyrimidine),8.26 (d, 1H, J = 5.2 Hz, H-6pyrimidine).13CNMR (CDCl3): delta 2.56 (s, 3H, SCH3),7.16 (d, 1H, J = 5.2 Hz, H-5pyrimidine),8.26 (d, 1H, J = 5.2 Hz, H-6pyrimidine).HPLC:Rt = 3.11min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,49844-90-8, its application will become more common.

Reference:
Article; Bendjeddou, Lyamin Z.; Loaec, Nadege; Villiers, Benoit; Prina, Eric; Spaeth, Gerald F.; Galons, Herve; Meijer, Laurent; Oumata, Nassima; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 696 – 709;,
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Pyrimidine – Wikipedia

Electric Literature of 934524-10-4, 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.934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C13H9Cl2N3O2S, molecular weight is 342.2, as common compound, the synthetic route is as follows.

A solution of 2,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.580 mmol), 3-aminobenzamide (83 mg, 0.61 mmol) and triethylamine (0.200 mL, 1.44 mmol) in dioxane (5 mL) was stirred at 1100C for 20 h. It was concentrated in vacuo. After the residue was acidified with HOAc ( 1 mL), it was purified by HPLC to give 3-(2-chloro-7-tosyl-7H- pyrrolo[2,3-d]pyrimidin-4-ylamino)benzamide (85 mg).

The chemical industry reduces the impact on the environment during synthesis 934524-10-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2009/131687; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C13H9Cl2N3O2S, 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. COA of Formula: C13H9Cl2N3O2S

Example 116; 2-[(2-{[1-(lambda/,lambda/-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-c/]pyrimidin-4-yl)amino]-6-fluoro-lambda/-methylbenzamide; Step A/Intermediate D4: 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7/-/-pyrrolo[2,3- c/]pyrimidin-4-yl}amino)-6-fluorobenzoic acid; A slurry of 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (50 g, 146 mmol) and 2-amino-6-fluorobenzoic acid (27.2 g, 175 mmol) (for instance from Acros Organics, Belgium) in iPrOH (1200 ml.) and 30 ml. of DIEA was heated to reflux. After 1 h, the solution turned a clear brown color, at which time about 450 ml_ of solvent were removed via distillation. The remaining mixture was treated with DIEA (90 ml.) and heated to reflux for 16 hours. The reaction mixture was then further concentrated by distilling more solvent off (400 ml. over 4 hours), then continued heating at reflux overnight. The resulting mixture was cooled to room temperature and concentrated under reduced pressure to obtain a thick oil which was diluted with EtOAc (1.3 L), then sequentially washed with a 1 N HCI solution (2×500 ml_), and a saturated NaHCOs solution (500 ml_). Further dilution of the separated organic layer with a saturated NaCI solution (500 ml.) led to the formation of a thick precipitate. The entire mixture was filtered and the solid was washed with Et2O. The solid was dried overnight in a vacuum oven at 60 0C to obtain 2-({2-chloro-7-[(4- methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid as a yellow solid (61.63 g, 92%). 1H NMR (400 MHz, DMSO-d6) delta ppm 2.37 (s, 3 H), 6.67 (d, J=3.85 Hz, 1 H), 6.71 – 6.81 (m, 1 H), 7.31 (td, J=8.33, 6.04 Hz, 1 H), 7.48 (d, J=8.24 Hz, 2 H), 7.74 (d, J=4.03 Hz, 1 H), 7.98 (d, J=8.42 Hz, 2 H), 8.36 (d, J=8.24 Hz, 1 H); ESIMS (M+H)+ = 461.06.

With the rapid development of chemical substances, we look forward to future research findings about 934524-10-4.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/20990; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia