Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 35265-83-9, 2,4-Dichloro-7-methylthieno[3,2-d]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, COA of Formula: C7H4Cl2N2S, blongs to pyrimidines compound. COA of Formula: C7H4Cl2N2S

Reference Example 24 2-Chloro-4-(1,3-dihydroxypropan-2-yl)amino-7-methylthieno[ 3,2-d]pyrimidine In 8 ml of DMF was dissolved 1.0 g (4.6 mmol) of 2,4-dichloro-7-methylthieno[3,2-d]pyrimidine, and then 977 mg (10.7 mmol) of 2-amino-1,3-propanediol was added dropwise to the resulting solution under ice cooling over 5 minutes. The reaction mixture was stirred at 0 C. for one hour and then allowed to resume room temperature, followed by stirring for one hour. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml*3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/2) to give 903 mg (yield: 72.3%) of the title compound. NMR (delta, DMSO-d6): 2.28 (3H, s), 3.52-3.61 (4H, m), 4.26-4.34 (1H, m), 4.73 (2H, t, J=6 Hz), 7.80 (1H, s), 7.90 (1H, d, J=8 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,35265-83-9, 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NAKASHIMA, YOSHIHARU; FUJITA, TAKASHI; HIZUKA, MICHIYO; IKAWA, HIROSHI; HIRUMA, TORU; US2001/6969; (2001); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 874676-81-0, 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. 874676-81-0, name is 5-Chloro-2-iodopyrimidine. A new synthetic method of this compound is introduced below.

A solution of 4-((l r,4r)-4-(4-(methylsulfonyl)phenoxy)cyclohexyloxy)piperidine hydrochloride (30 mg, 0.077 mmol), 5-chloro-2-iodopyrimidine (28 mg, 0.12 mmol), and Et3N (20 mg, 0.20 mmol) in IPA (1 mL) was stirred for 3 h at 85 C. The reaction was cooled to room temperature to form a precipitate. The solid was filtered, washed with H20, 1 N HC1, IPA, and dried to give the title compound (30 mg). LCMS m/z = 466.2 [M+H]+; lU NMR (400 MHz,CDC13) delta 1.45-1.65 (m, 6H), 1.84-1.92 (m, 2H), 1.97-2.04 (m, 2H), 2.08-2.16 (m, 2H), 3.02 (s, 3H), 3.38-3.46 (m, 2H), 3.54-3.60 (m, IH), 3.63-3.70 (m, IH), 4.18-4.26 (m, 2H), 4.37-4.45 (m, IH), 6.99 (d, J = 8.8 Hz, 2H), 7.84 (d, J = 8.8 Hz, 2H), 8.20 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,874676-81-0, 5-Chloro-2-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; BUZARD, Daniel J.; LEHMANN, Juerg; NARAYANAN, Sanju; YUE, Dawei; WO2011/127051; (2011); A1;,
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Pyrimidine – Wikipedia

Reference 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 a solution of 2,4,6-trichloro-pyrimidine-5-carbaldehyde (3.7 g, 17.5 mmol) in EtOH (50 mL) cooled to -78° C. was added methyl hydrazine (0.93 mL, 17.5 mmol) and TEA (8 mL). The mixture was stirred for 30 minutes at -78 C then 2 hr at 0 C. The solution was concentrated in vacuo without heating. To the reduced volume solution was added EtOAc and the solution washed with a sat NaHCO3 solution and concentrated in vacuo without heating. Filtration over a small silica gel plug (2:1 EtOAc:Hex) and concentration afforded the desired product as a yellow solid. It should be noted that the reaction with aromatic hydrazine compounds can be conducted at 0° C.

According to the analysis of related databases, 50270-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2009/98086; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 31519-62-7 ,Some common heterocyclic compound, 31519-62-7, molecular formula is C5H4N2O2, 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.

114. f+)-2-f(3.,4-trans)-4-methyl-l-fpyrimi(iine-2-carbonyl)pyrroli(iin-3- yl)-7-ftetrahvdro-2H-pyran-4-yl)imidazo[5,l- 1 [l,2,41triazin-4f3H -one [1073] To a stirred solution of (+)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l: ][l,2,4]triazin-4(3H)-one (75 mg, 0.24 mmol) in DMF (5 mL) were added EDCI (70 mg, 0.37 mmol), HOBt (50 mg, 0.37 mmol), DIPEA (95 mg, 0.74 mmol) and pyrimidine-2-carboxylic acid (40 mg, 0.32 mmol) at 0 C under inert atmosphere. The resulting reaction mixture was allowed to warm to room temperature and stirred for 8 h. The reaction mass was diluted with water (100 mL) and extracted with DCM (3 x 50 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford (+)-2-((3,4-trans)-4-methyl-l-(pyrimidine-2-carbonyl)pyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l: ][l,2,4]triazin-4(3H)-one (40 mg, 40%) as an off-white solid. 1H-NMR (DMSO d6, 400 MHz): delta 11.95 (bs, 1H), 8.97 (d, 2H), 6.69- 6.58 (m, 2H), 3.98-3.84 (m, 4H), 3.65-3.57 (m, 4H), 3.22-3.27 (m, 2H), 2.68-2.61 (m, 1H), 1.90-1.84 (m, 4H), 1.08 (d, 3H); Mass (ESI): 410 [M++l] LC-MS: 98.92%; 410.3 (M++l); (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 1.85 min. 0.05% TFA in water: ACN; 0.8 ml/min); UPLC (purity): 98.76%; (column; Eclipse XDB C- 18, (150×4.6 mm, 5.0mu); RT 8.23 min. 5mM NH4OAc (Aq): ACN; 1.0 ml/min; Chiral HPLC: 99%, R, = 37.69 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) n- Hexane (B) DCM:MeOH (80:20) (A: B : 80:20); flow Rate: 1.00 mL/min); Optical rotation [a]D2: +12.17 (c = 0.25, DCM). TLC: 10% MeOH/DCM (Rf: 0.5).

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. 31519-62-7, 2-Pyrimidinecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 1197953-49-3 ,Some common heterocyclic compound, 1197953-49-3, molecular formula is C12H12Cl2N3OP, 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.

AP26113 intermediate (2g, 6.3mmol) was added sequentially in a standard microwave reaction tube at room temperature.SIAIS 1197129 (2.4 g, 7.8 mmol), Pd(OAc) 2 (176 mg, 0.78 mmol), Xantphos (810 mg, 1.4 mmol),cesium carbonate (6.4 g, 19.6 mmol), 30 mL DMF, followed by argon exchange, microwave reaction at 110 C for 1.5 h. TLC detection reactionAfter the bundle, the mixture was filtered through silica gel, water-purified, ethyl acetate, washed with water, dried over anhydrous sodium sulfate,Methanol and water gave a reddish brown solid (900 mg) directly to the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1197953-49-3, its application will become more common.

Reference:
Patent; ShanghaiTech University; Yang Xiaobao; Jiang Biao; Song Xiaoling; Lin Haifan; Sun Ning; Chen Jinju; Qiu Xing; Ren Chaowei; Kong Ying; (232 pag.)CN109912655; (2019); 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 62458-96-2, name is 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. name: 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one

31-A. 4-Oxo-4,5,6,8-tetrahydro-3H-pyrido[3,4-Patent; NOVARTIS AG; ARTMAN III, Gerald David; ELLIOTT, Jason Matthew; JI, Nan; LIU, Donglei; MA, Fupeng; MAINOLFI, Nello; MEREDITH, Erik; MIRANDA, Karl; POWERS, James J.; RAO, Chang; WO2010/66684; (2010); A2;,
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Pyrimidine – Wikipedia

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.131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, molecular weight is 320.73, as common compound, the synthetic route is as follows.Safety of (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate

To a solution of methyl (E)-2-{2-[6-chloropyrimidin~4-yloxy]phenyl} -3-methoxyacrylate (64.4g; prepared as described in WO 92/08703) in cyclohexanone (approximately 80g) was added 2-cyanophenol (26.6g) and cyclohexanone (26.6g). The mixture was heated to 5O0C and DABCO (0.2g) in cyclohexanone (2g) and potassium carbonate (42.4g) were charged. The reaction was heated to 9O0C and held for three hours. The temperature was adjusted to 50-600C and hot water (88g) added, stirred for 15 minutes, and the aqueous phase separated. Analysis of the cyclohexanone layer gave a 91.3% yield of methyl (E)- 2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (azoxystrobin). Cyclohexanone was removed by vacuum distillation, and to the distillation residues at 8O0C was added methanol (59g). The methanol solution was cooled slowly to 0-50C, filtered and the cake washed with methanol (2×15.8g) to give, after drying, methyl (E)- 2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (87.0% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA LIMITED; WO2006/114572; (2006); A2;,
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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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, molecular formula is C5H5ClN2S, 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. Application In Synthesis of 4-Chloro-2-(methylthio)pyrimidine

A mixture of 4-chloro-2-(methylthio)pyrimidine (102.6 g, 0.639 mol), 3-phenyl-1H-pyrazole-4-carbaldehyde (100.0 g, 0.581 mol), potassium carbonate (160.5 g, 1.162 mol), and dimethylformamide (700 mL) was stirred at 40-50 for 2 hours. Purified water (1.6 L) was slowly added to the reaction mixture, which was then stirred at room temperature for 2 hours. The resulting solid was filtered and then driedinvacuoto obtain 154.0 g of the titled compound. (Yield: 89.5%[78]1H-NMR(400MHz, CDCl3) delta 10.10(s, 1H), 9.20(s,1H), 8.65(d, 1H), 7.84-7.86(m, 2H), 7.67-7.71(m, 3H), 2.65(s, 3H)

With the rapid development of chemical substances, we look forward to future research findings about 49844-90-8.

Reference:
Patent; YUHAN CORPORATION; OH, Sang-Ho; KHOO, Ja-Heouk; LIM, Jong-Chul; LEE, Doo-Byung; LEE, Jung-Ae; LEE, Jun-Sup; JU, Hyun; SHIN, Woo-Seob; JEON, Sang-Seol; (24 pag.)WO2019/22486; (2019); A1;,
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Pyrimidine – Wikipedia

Reference of 22536-66-9 ,Some common heterocyclic compound, 22536-66-9, molecular formula is C5H4ClN3O, 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.

Example 261 N-[10,ll-dimethyl-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02’6]dodeca- l(12),6,8,10-tetraen-3-yl]-2-[(2-methoxyethyl)amino]pyrimidine-4-carboxamide (ABR 239626) To a stirred solution of 2-chloropyrimidine-4-carboxamide, available via a literature method: PCT Int. AppL, 2001068612 (330 mg, 2.08 mmol) in DMF (6 mL) was added methyl 3,3,3- trifiuoro-2-oxopropanoate (355 mu, 3.47 mmol) followed by pyridine (170 mu, 2.08 mmol) under nitrogen. The reaction was stirred at room temperature for 2 h. Thionyl chloride (150 mu, 2.08 mmol) was added at 0C. The reaction was stirred for 1 h at 0C and then concentrated. The residue was filtered through a short pad of silica, eluting with DCM, under nitrogen. The filtrate was concentrated, and the acyl intermediate that remained was dissolved in DMF (5 mL) under nitrogen. The solution of acyl intermediate was added to a solution of 5,6-dimethyl-lH-l ,3- benzodiazol-2 -amine (280 mg, 1.74 mmol) in DMF (8 mL) followed by triethylamine (280 2.08 mmol). The reaction mixture was stirred for a further 16 h and then concentrated. The residue was dissolved in EtOAc (50 mL) and washed with water (3 x 50 mL) and brine (2 x 50 mL) and then dried (MgSO_i), filtered and concentrated to afford 2-chloro-N-[10,l 1 -dimethyl-4- oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3- yl]pyrimidine-4-carboxamide. (260 mg, 15%). m/z = 424.95 (MH)+. A sealable tube was charged with a portion of 2-chloro-N-[10,l 1 -dimethyl-4-oxo-3- (trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3-yl]pyrimidine-4- carboxamide (250 mg, 0.35 mmol), 2-methoxyethan- 1 -amine (92 muL·, 1.06 mmol), K2C03 (150 mg, 1.06 mmol) and DMF (5 mL). The tube was flushed with nitrogen, sealed and stirred at 100C for 6 h. Then reaction mixture was concentrated and the resulting residue was diluted with EtOAc (20 mL) and water (20 mL). The aqueous phase was extracted with EtOAc (2 x 10 mL). The combined organic extracts were washed with 10 % citric acid (aq) (2 x 20 mL) and brine (20 mL) and then dried (MgS04), filtered and concentrated. The crude product was purified by automated reverse phase HPLC (low pH Method A) to afford the title compound as a white solid (50 mg, 31 %).

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. 22536-66-9, 2-Chloropyrimidine-4-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTIVE BIOTECH AB; WELLMAR, Ulf; LIBERG, David; EKBLAD, Maria; BAINBRIDGE, Marie; EAST, Stephen; HARGRAVE, Jonathan; PREVOST, Natacha; WO2015/177367; (2015); A1;,
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Related Products of 696-82-2, 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 696-82-2, name is 2,4,6-Trifluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(1) 34.1 parts of H acid was dissolved in 200 parts of water,Add 10% sodium carbonate solution to adjust the pH to 7,Total dissolved, then 13.5 parts of trifluoropyrimidine at 20 C,Condensed at pH 5 for 3 to 4 hours,No H acid when the end point, obtained condensation products; (2) take 12.3 parts of para-amino-anisidine diazonium salt, and the condensation product obtained in step (1) at 15 C, a pH of 6Under the conditions of coupling reaction 5h, to give compound A.

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 696-82-2, 2,4,6-Trifluoropyrimidine.

Reference:
Patent; Jiangsu Demeike Chemical Co., Ltd.; Wang Xiaojun; (7 pag.)CN106398303; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia