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.675-11-6, name is 4,6-Difluoropyrimidin-2-amine, molecular formula is C4H3F2N3, molecular weight is 131.0835, as common compound, the synthetic route is as follows.category: pyrimidines

EXAMPLE 5 Preparation of 6-allyloxy-2-amino-4-fluoropyrimidine (Variant A) STR13 1.14 g (0.0382 mol) of 80% sodium hydride (emulsion in linseed oil) were added at 25 C. under a nitrogen atmosphere to 70 ml of allyl alcohol. To the clear solution obtained after stirring at 40 C. for 20 minutes were added 5.0 g (0.0382 mol) of 2-amino-4,6-difluoropyrimidine, and the mixture was then stirred at 97 C. for 1.5 hours. To work up, the excess alcohol was removed by distillation under reduced pressure, the residue was taken up in methylene chloride, and the solution was washed with water, dried over magnesium sulfate and then freed of solvent. The viscous oil obtained in this way crystallized on trituration with n-pentane. 4.6 g (71.2% of theory) of the title compound of melting point 62-66 C. were obtained after filtering off, washing with water and drying.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,675-11-6, 4,6-Difluoropyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; BASF Aktiengesellschaft; US5011927; (1991); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 14248-01-2 ,Some common heterocyclic compound, 14248-01-2, molecular formula is C5H5BrN2O, 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.

Step 2: 5-(4-Amino-3,5-dimethylphenyl)-1-methylpyrimidin-2(1H)-one [0768] The title compound is prepared from 5-bromo-1-methylpyrimidin-2(1H)-one and 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline following a procedure analogous to that described in Step 2 of Intermediate 62. The mixture is stirred for 12 hours at 70 C. LC (method 9): tR=0.63 min; Mass spectrum (ESI+): m/z=230 [M+H]+.

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. 14248-01-2, 5-Bromo-1-methylpyrimidin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; US2013/252937; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 209959-33-1, name is 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine

Step B: A mixture of 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (3.0 g, 8.0 mmol), dimethylzinc (1.2 M×8.0 mL, 9.6 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (130 mg, 0.16 mmol) in 1,4-dioxane (30 mL) was stirred at 110 C. for 16 h under Argon. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated NH4Cl, water and brine. The organic layer was dried over NaSO4, concentrated and purified by silica gel column chromatography (0-35% EtOAc in hexanes) to give a white solid, which was dissolved in trifluoroacetic acid (5.0 mL). After 5 min, the solvent was removed and the residue was partitioned between ethyl acetate and an aqueous saturated NaHCO3 solution. The organic layer was dried over NaSO4, filtered and concentrated to give the title compound (0.7 g, 80%) as a white solid. MS m/z 110.1 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 209959-33-1.

Reference:
Patent; PTC Therapeutics, Inc.; F. Hoffmann-La Roche AG; Woll, Matthew G.; Chen, Guangming; Choi, Soongyu; Dakka, Amal; Huang, Song; Karp, Gary Mitchell; Lee, Chang-Sun; Li, Chunshi; Narasimhan, Jana; Naryshkin, Nikolai; Paushkin, Sergey; Qi, Hongyan; Turpoff, Anthony A.; Weetall, Marla L.; Welch, Ellen; Yang, Tianle; Zhang, Nanjing; Zhang, Xiaoyan; Zhao, Xin; Pinard, Emmanuel; Ratni, Hasane; (317 pag.)US9617268; (2017); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 313339-35-4, 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. 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, 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.

Reference Example 70 Production of ethyl 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylate To a solution of the compound of Reference Example 69 (4.02 g, 18 mmol), amidosulfuric acid (3.50 g, 36 mmol), tert-butanol (72 mL), THF (72 mL) and water (36 mL) was added a solution of sodium chlorite (2.03 g, 18 mmol) in water (36 mL) at -10C, and the mixture was stirred for 10 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with 1% aqueous sodium thiosulfate solution and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid as a crude product. To a solution of this crude product in THF (50 mL) were added oxalyl chloride (2.36 mL, 27 mmol) and DMF (1 drop), and the mixture was stirred at room temperature for 1 hr. Water was added thereto, and the mixture was extracted twice with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. To the residue were added ethanol (50 mL) and triethylamine (3.76 mL, 27 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted twice with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=99:1?90:10) to give the title compound (3.28 g, 68%) as a pale-yellow oil. 1H NMR (300 MHz, CDCl3) delta:1.41 (3 H, t, J = 7.2 Hz), 2.59 (3 H, s), 4.45 (2 H, q, J = 7.1 Hz).

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 313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2471793; (2012); A1;,
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. 5267-07-2, name is 5-Pyrimidineacetic acid, molecular formula is C6H6N2O2, 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. Recommanded Product: 5-Pyrimidineacetic acid

General procedure: A flask was charged with 657 (70 mg, 0.155 mmol), 5-pyrimidineacetic acid (22 mg, 0.162 mmol) in DMF (1 ml) at 0 C was added HOBT (44 mg, 0.326 mmol) followed by EDCI (78 mg, 0.408 mmol). The resulting mixture was slowly warmed up to room temperature and stirred for overnight before it was quenched by addition of ice water (~5 mL). The white precipitate was collected by suction filtration, rinsed with more water. The crude material was purified by silica gel chromatography eluting with 0- 6% MeOH in dichloromethane to afford 675. 1H NMR (300 MHz, DMSO-d6) delta 12.75 (s, 1H), 11.32 (s, 1H), 9.11 (s, 1H), 8.76 (s, 1H), 8.22-8.19 (d, J= 9.12 Hz, 1H), 7.59-7.26 (m, 6H), 3.94 (s, 2H), 3.87 (s, 2H), 3.01 (bs, 2H), 2.90 (bs, 2H), 1.73 (bs, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 5267-07-2.

Reference:
Patent; CALITHERA BIOSCIENCES INC.; LI, Jim; CHEN, Lijing; GOYAL, Bindu; LAIDIG, Guy; STANTON, Timothy, Friend; SJOGREN, Eric, Brian; WO2013/78123; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 199678-12-1 ,Some common heterocyclic compound, 199678-12-1, molecular formula is C11H8N2O2, 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.

Under an argon atmosphere, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.87 g, 9.76 mmol) and dimethylaminopyridine (2.48 g, 20.3 mmol) were added to a solution of compound 18 (2.00 g, 8.13 mmol) and 4-pyrimidin-2-ylbenzoic acid (2.00 g, 10.0 mmol) in dehydrated N,N-dimethylformamide (30 mL) at 0 C. The reaction mixture was left to stand overnight, then poured into ice water and stirred for 0.5 h at 0 C. The precipitate was collected by filtration and dissolved in ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated to afford 2.80 g (88%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 9.14 (t, J = 5.6 Hz, 1H), 8.94 (d, J = 4.8 Hz, 2H), 8.49 (d, J = 8.8 Hz, 2H), 8.17 (dd, J = 9.2, 2.8 Hz, 1H), 8.07-8.04 (m, 3H), 7.49 (t, J = 4.8 Hz, 1H), 7.22 (d, J = 8.8 Hz, 1H), 4.52 (d, J = 5.6 Hz, 2H), 4.14 (t, J = 6.4 Hz, 2H), 1.84 – 1.75 (m, 2H), 1.01 (t, J = 7.4 Hz, 3H).

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. 199678-12-1, 4-Pyrimidin-2-yl-benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ohashi, Masao; Gamo, Kanae; Tanaka, Yuta; Waki, Minoru; Beniyama, Yoko; Matsuno, Kenji; Wada, Jun; Tenta, Masafumi; Eguchi, Jun; Makishima, Makoto; Matsuura, Nobuyasu; Oyama, Takuji; Miyachi, Hiroyuki; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 53 – 67;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 56621-91-1, 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. 56621-91-1, name is 5-Amino-2-bromopyrimidine. A new synthetic method of this compound is introduced below.

To a stirred solution of compound 2-bromopyrimidin-5-amine (950 mg, 5.46 mmol), 3-((fert- butoxycarbonyl)amino)propanoic acid (1.54 g, 8.14 mmol) in DCM (25 mL) was added TEA (3.02 mL, 21.84 mmol) and T3P (3.47 g, 10.92 mmol) at 0 C and the reaction mixture was stirred at rt for 24 h. The mixture was diluted with DCM and washed with sat NaHCOs, the separated organic layer was dried over anhydrous feSCk The organic layer was concentrated under reduced pressure and the obtained crude compound was purified by flash column chromatography using 45 % of ethyl acetate in pet ether as an eluent to obtain the title compound (900 mg, 47%). (0705) LC-MS (method 1): R. = 1.19 min; m/z = 344.82 (M+H++2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56621-91-1, its application will become more common.

Reference:
Patent; ORYZON GENOMICS, S.A.; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; SALAS SOLANA, Jorge; (129 pag.)WO2018/219478; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 60703-46-0, 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. 60703-46-0, name is 2,4,6-Trichloro-5-methoxypyrimidine, molecular formula is C5H3Cl3N2O, 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 an atmosphere of nitrogen a solution of 2,4,6-trichloro-5-methoxy-pyrimidine (4.0 g, 18.7 mmol) in DCM (200 mL) was cooled to 0 C. and treated with boron tribromide (6.6 mL, 65 mmol) dropwise. After stirring for 18 hours at RT the reaction mixture was cooled and diluted with methanol (25 mL, CARE, EXOTHERM.) and the reaction mixture diluted with water (200 mL). The aqueous layer was extracted with DCM and the combined organic extracts dried (Na2SO4) and concentrated in vacuo to give 2,4,6-Trichloro-5-hydroxy-pyrimidine as a pale tan solid (2.55 g, 71%). 13C NMR (DMSO-d6): 149.23 (C), 145.25 (C), 145.08 (C). LCMS (Method C): RT=2.65/2.77. [M-H]+ 197/199.

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 60703-46-0, 2,4,6-Trichloro-5-methoxypyrimidine.

Reference:
Patent; Genentech, Inc.; Heald, Robert Andrew; McLean, Neville James; US2014/65136; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 60703-46-0, 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 60703-46-0 as follows.

EXAMPLE 5 Preparation of 2-morpholino-5-methoxy-4,6-dichloropyrimidine 150 parts by volume of benzene, 34 parts of 5-methoxy-2,4,6-trichloro-pyrimidine and 17.7 parts of N-methyl-morpholine are introduced into a reactor. The mixture is heated under reflux for 3 hours, then filtered and the solution is evaporated. The residue obtained is recrystallized from ethanol. 30 parts of 2-morpholino-5-methoxy-4,6-dichloro-pyrimidine of melting point 116C are thus obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60703-46-0, its application will become more common.

Reference:
Patent; Societe Generale de Recherches et d’Applications Scientifiques “Sogeras”; US3984411; (1976); A;,
Pyrimidine | C4H4N2 – PubChem,
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. 87026-45-7, name is 4-Chloro-5-methoxy-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. name: 4-Chloro-5-methoxy-2-(methylthio)pyrimidine

Step A: 4-F5- (5-METHOXY-2-METHYLSULFANYL-PVRIMIDIN-4-V -THIOPHEN-2-YL]-2-METHYL-BUTAN-2-OL A solution OF 2-METHYL-4-THIOPHEN-2-YL-BUTAN-2-OL (340 mg, 2 mmol)-synthesis see Step A of Example 1-in 20 ml of THF was treated with LDA (2M in THF/HEPTANE/ETHYLBENZENE, 5 ML, 10 mmol) at-78 C under nitrogen and the mixture was stirred for 5 minutes. Then, trimethylborate (1.1 ml, 10 mmol) was added in one portion and the cooling bath was removed. After 15 minutes, the mixture was quenched with 50 ml of saturated ammonium chloride solution and extracted twice with ether. The aqueous layer was then acidified with 2N-HCI and extracted once more with ether. The combined organic extracts were washed with brine and evaporated. This crude boronic acid was redissolved in 10 ml of DME and added to a stirred suspension 4-chloro-5-methoxy-2-methylsulfanyl-pyrimidine (190 mg, 1 mmol), Pd (PPH3) 4 (23 mg, 0.02 mmol), 20 ml of DME and 3 ml of a 10% solution of sodium bicarbonate. This mixture was then kept at reflux (100 C heat bath) for 90 minutes. After cooling, most of the DME was evaporated and the crude was partitioned between water and ether. The organic layer was separated, washed with 0. 2N-HCI, water and brine, dried over sodium sulfate and evaporated. The crude was purified by chromatography on silicagel (EtOAc/hexane: 1/1) to give 4- [5- (5- METHOXY-2-METHYLSULFANYL-PYRIMIDIN-4-YL)-THIOPHEN-2-YL]-2-METHYL-BUTAN-2-OL. Yield: 275 mg (85%).

The synthetic route of 87026-45-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMHBH; WO2004/89913; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia