Pyrimidines

Electric Literature of 31058-83-0 , The common heterocyclic compound, 31058-83-0, name is 6-Chloro-N,N-dimethylpyrimidin-4-amine, molecular formula is C6H8ClN3, 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 mixture ofN-(cis-4-bromo-2-trifluoromethoxy-benzyl)-cyclohexane-1, 4- diamine (466 mg), (6-chloro-pyrimidin-4-yl) -dimethyl-amine (200 mg), and ethylene glycol (0.5 mL) was stirred at reflux for 4 hr in a sealed tube. The mixture was poured into saturated aqueous NaHC03 and the aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromatography (NH-silica gel, 50% EtOAc in hexane and silica gel, 501-‘o MeOH in CHCl3) to give N’- (cis-4- { [4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N, N-dimethylpyrimidine-4, 6-diamine. To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. The residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give N’-(cis-4-{[4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N,N-dimethylpyrimidine-4, 6-diamine dihydrochloride (67 mg). ESI MS m/e 488, M (free) + H+ ;’H NMR (300 MHz, CDC13) 8 1.64-1. 86 (m, 2 H), 1.96- 2.34 (m, 8 H), 2. 98-3.44 (m, 8 H), 4.27 (s, 2 H), 7.40-7. 59 (m, 3 H), 8.06-8. 24 (m, 2 H).

The synthetic route of 31058-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
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Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2434-53-9, name is 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione

Mixture of 6-amino-1-methyl-pyrimidine -2,4 (1H, 3H) – dione(5.46g, 40.0mmol) and bromo succinimide (7.56g, 42.0mmol) in acetonitrile (100 mL) solution was heated to reflux under nitrogen protection for 1.5 hours. The reaction was cooled to room temperature, filtered, (20 mL) and washed to remove the solvent, the resulting solid was washed with water, and dried to give 6-amino-5-bromo-1-methyl-pyrimidine -2,4 (1H, 3H)-dione (8.6g, white solid), yield: 98%

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 2434-53-9, 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Sichuan Gooddoctor Pharmaceutical Group Co., Ltd.; Wu, Lingyun; Zhang, Peng; Zhang, Li; Li, Jian; Chen, Shuhui; Geng, Funeng; Chen, Yongmei; Liu, Bin; Ma, Xiuying; (109 pag.)CN105566324; (2016); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 22536-63-6, name is 2-Chloro-4-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloro-4-methoxypyrimidine

Reference Example 24 N-(4-Iodophenyl)-4-methoxy-N-methylpyrimidin-2-amine [Show Image] (1) Under an argon atmosphere, sodium hydride (100 mg) was added to a solution of 4-iodoaniline (220 mg) and 2-chloro-4-methoxypyrimidine (145 mg) in anhydrous DMF (10 ml), and the resulting mixture was stirred at 125C for 21 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by extracting the resulting mixture with ethyl acetate. Organic layer was washed twice with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate = 10/1) to obtain N-(4-iodophenyl)-4-methoxypyrimidin-2-amine (46 mg).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 22536-63-6, 2-Chloro-4-methoxypyrimidine.

Reference:
Patent; Toray Industries, Inc.; EP2042171; (2009); A1;,
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Pyrimidine – Wikipedia

Application of 1749-68-4, 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.1749-68-4, name is 6-Chloro-2-methylpyrimidin-4-amine, molecular formula is C5H6ClN3, molecular weight is 143.57, as common compound, the synthetic route is as follows.

The 6-amino-4-(1-indolinyl)-2-methylpyrimidine was obtained as a solid, m.p. 209-210 C., in a similar number to that described for the analogous intermediate in Example 51 by reaction of 6-amino-4-chloro-2-methylpyrimidine with indoline.

The chemical industry reduces the impact on the environment during synthesis 1749-68-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Imperial Chemical Industries Plc; US5223505; (1993); A;,
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Pyrimidine – Wikipedia

Related Products of 54326-16-8, 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. 54326-16-8, name is 5-Chloropyrimidin-2(1H)-one, molecular formula is C4H3ClN2O, 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.

I. N-(5-tert-butyl-isoxazol-3-yl)-N’-{4-[6-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea hydrochloride [Compound B12] was also prepared by first preparing the benzothiazole starting material, 5 methoxy-benzothiazol-2-yl-amine: To prepare the 5-methoxy-benzothiazol-2-ylamine starting material: To a suspension of (3-methoxy-phenyl)-thiourea (1.822 g, 10 mmol) in CH2Cl2 (20 mL) at 0 C. was added dropwise a solution of bromine (1.76 g, 11 mmol) in 10 ml of trichloromethane over a period of thirty minutes. The reaction was stirred for 3 hours at room temperature then heated to 3 hours to reflux for one hour. The precipitate was filtered and washed with dichloromethane. The solid was suspended in saturated NaHCO3 and extracted with CH2Cl2. The extract was dried over MgSO4 and concentrated to give a white solid (1.716 g, 95%). To prepare the 2-amino-benzothiazol-5-ol: To a suspension of 5-methoxy-benzothiazol-2-ylamine in 16 mL of 48% HBr/H2O was heated to 105 C. in an oil bath for 10 hours. After the reaction was cooled to room temperature, the precipitate was collected by filtration and washed with acetone. The filtrate was suspended in saturated NaHCO3 and extracted with CH2Cl2. The extract was dried over MgSO4 and concentrated to give a white solid (0.986 g, 63%). N-(5-tert-butyl-isoxazol-3-yl)-N’-{4-[6-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea hydrochloride 2-amino-benzothiazol-5-ol from the previous step and following the method described in 1H NMR (DMSO-d6) ? 11.1 (br, 1H), 9.69 (br, 1H), 9.28 (br, 1H), 8.71 (s, 1H), 7.97 (d, 1H), 7.79 (d and s, 3H), 7.56 (d, 2H), 7.13 (dd, 1H), 6.53 (s, 1H), 4.56 (t, 2H), 3.98 (m, 2H), 3.82 (t, 2H), 3.65 (m, 2H), 3.55 (m, 2H), 3.25 (m, 2H), 1.31 (s, 9H); LC-MS: ESI 561 (M+H)+. [Compound B12]

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 54326-16-8, 5-Chloropyrimidin-2(1H)-one.

Reference:
Patent; Bhagwat, Shripad; Chao, Qi; Grotzfeld, Robert M.; Patel, Hitesh K.; Sprankle, Kelly G.; US2007/232604; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 108831-66-9, 6-Methyl-3H-thieno[2,3-d]pyrimidin-4-one, 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, HPLC of Formula: C7H6N2OS, blongs to pyrimidines compound. HPLC of Formula: C7H6N2OS

General procedure: A mixture of thienopyrimidinone (0.01 mol), POCl3 (11 mL) and PCl5 (1.5 g) was quickly heated to 105 C and boiled for 5-6 h. The solvent was evaporated. Dry product was dissolved in methylene chloride (12 mL) and neutralized by cold solution of NaOH (0.5 N). The organic phase was separated and dried over Na2SO4, filtered, and then solvent was evaporated in vacuum. The residue was crystallized from isopropyl alcohol. Yield 80%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,108831-66-9, 6-Methyl-3H-thieno[2,3-d]pyrimidin-4-one, and friends who are interested can also refer to it.

Reference:
Article; Ostrynska, Olga V.; Balanda, Anatoliy O.; Bdzhola, Volodymyr G.; Golub, Andriy G.; Kotey, Igor M.; Kukharenko, Olexander P.; Gryshchenko, Andrii A.; Briukhovetska, Nadiia V.; Yarmoluk, Sergiy M.; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 148 – 160;,
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Pyrimidine – Wikipedia

Related Products of 116247-92-8 ,Some common heterocyclic compound, 116247-92-8, molecular formula is C9H11N3O, 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 mixture of 3-amino-5- (5-methyl-lH-pyrazol-4- yl) thiophene-2-carboxamide (111 mg, 0.50 mmol) , l-(2- pyrimidinyl) -piperidin-4-one (266 mg, 1.50 mmol), CSA (11.6 mg, 0.05 mmol), MgSO4 (120 mg, 1.00 mmol) and DMA (4 mL) was stirred at 1000C for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with 3:1 EtOAc/THF, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, EtOAc to 80:20 EtOAc/MeOH) . The obtained yellow solid was triturated with MeOH/EtOAc and collected by filtration to afford the title compound (141 mg, 74%) as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) 6 1.74-1.98 (4H, m) , 2.34-2.40 (3H, m) , 3.55-3.64 (2H, m) , 4.12-4.20 (2H, m) , 6.60-6.63 (2H, m) , 7.24 (IH, br s) , 7.52 (IH, br s) , 7.71 (0.67H, br s) , 8.08 (0.33H, br s) , 8.35-8.37 (2H, m) , 12.79 (0.33H, br s) , 12.87 (0.67H, br s) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116247-92-8, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; OGURO, Yuya; KURASAWA, Osamu; WO2010/101302; (2010); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 63931-21-5, Adding some certain compound to certain chemical reactions, such as: 63931-21-5, name is 5-Bromo-2,4,6-trichloropyrimidine,molecular formula is C4BrCl3N2, 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 63931-21-5.

5-Bromo-2,4,6-trichloropyrimidine (1.30 g, 4.96 mmol) and 3-(trifluoromethyl)- bicyclo[l.l. l]pentan-l- amine hydrochloride (985 mg, 4.99 mmol) were suspended in acetonitrile (6.5 mL) and N,N-diisopropylethylamine (1.55 g, 2.1 mL, 12 mmol) was added at room temperature. The resulting yellow solution was stirred for 7 h at room temperature. After that, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 80 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to yield, after drying in vacuo (40C, 5 mbar), the title compound as an off-white solid (1.487 g, 80%). HPLC (method LCMS_fastgradient) tR = 1.50 min. 1H NMR (CDC13, 300 MHz): delta 2.46 (s, 6 H), 6.10 (br s, 1 H). MS (ES+) m/z 375.9, 377.9, 379.8 [M+H, Br & 2 CI isotopes].

According to the analysis of related databases, 63931-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; STEINER, Sandra; (89 pag.)WO2018/11164; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate, 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, name: Methyl 2-chloropyrimidine-5-carboxylate, blongs to pyrimidines compound. name: Methyl 2-chloropyrimidine-5-carboxylate

A solution of methyl 2-chloropyrimidine-5-carboxylate (200 mg, 1.16 mmol) in dichloromethane (4.00 mL) was added to a stirred solution of 1-cyclopropyl-1,4-diazepane (247 mg, 1.16 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (0.902 mL, 5.22 mmol) in dichloromethane (4.00 mL) at 25 C. The resulting solution was stirred at ambient temperature for 18 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (20 mL) and the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford methyl 2-(4-cyclopropyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate (312 mg, 97%) as a cream solid. This was used directly with no further purification. 1H NMR (399.9 MHz, DMSO-d6) delta 0.28-0.31 (2H, m), 0.40-0.45 (2H, m), 1.80-1.84 (2H, m), 1.85-1.89 (1H, m), 2.71 (2H,m), 2.85-2.88 (2H, m), 3.81 (3H, s), 3.82-3.88 (4H, m), 8.79 (2H, s). MS: m/z 277 (MH+)

The synthetic route of 287714-35-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 41103-17-7, 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. 41103-17-7, name is Ethyl 4-chloropyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

2.1 g of the compound obtained in step 2) above and 2.64 g of 3-chloro-4- (pyridin-2-ylmethoxy)benzenamine were dissolved in 20 mL of 2-propanol, and the mixture was stirred for 3 hours. After the reaction was completed, the resulting solution was cooled to room temperature and distilled under a reduced pressure. The resulting residue was subjected to column chromatography (ethyl acetate : dichloromethane: methanol = 7 : 7 : 1) to obtain the title compound (2.0 g).1H-NMR (300MHz, CDC13) delta 10.32 (s, 1H), 9.01 (s, 1H), 8.79 (s, 1H), 8.60 (d, 1H), 7.82 (d, 1H), 7.75 (t, 1H), 7.73 {d, 1H), 7.43 (dd, 1H), 7.01 (dd, 1H), 5.29 (s, 2H), 4.34 (m, 2H), 1.26 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,41103-17-7, its application will become more common.

Reference:
Patent; HANMI HOLDINGS CO., LTD.; CHA, Mi Young; KIM, Mi Ra; KANG, Seok Jong; KIM, Se Young; JUNG, Young Hee; LEE, Kwang Ok; SONG, Ji Yeon; KIM, Young Hoon; KIM, Eun Young; KIM, Maeng Sup; WO2011/99764; (2011); A2;,
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