Pyrimidines

Reference of 2927-71-1, Adding some certain compound to certain chemical reactions, such as: 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine,molecular formula is C4HCl2FN2, 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 2927-71-1.

To a solution of 1.0M methylmagnesium bromide in tetrahydrofuran (270 ml) at 0C under nitrogen was added 2,4-dichloro-5-fluoropyrimidine (30 g) in 1,2- dimethoxyethane (90 ml) dropwise maintaining the temperature below 15C. The resulting solution was stirred at ~15C for one hour then cooled to 0C. A solution of triethylamine (25 ml) in dry tetrahydrofuran (40 ml) was added maintaining the temperature at ~5C, followed by a solution of iodine (45.6 g) in dry tetrahydrofuran (140 ml) maintaining the temperature below 15C. The reaction was quenched with water (400 ml) maintaining the temperature below 25C and treated with 5N aqueous hydrochloric acid solution (30 ml). The mixture was extracted with diethyl ether (2 x 500 ml) and the combined organic layer was washed with 2% w/w aqueous sodium metabisulfite (400 ml) and water (400 ml) then dried (MgS04) and evaporated. The residue was purified by silica gel column chromatography (gradient from 0 to 5% ethyl acetate / hexane) to afford the title compound (16.8 g) as an orange oil which was used in the next step without further purification. 1H-NMR (400 MHz, CDC13) delta (ppm): 2.57 (d, J=2.81 Hz, 3 H)

According to the analysis of related databases, 2927-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HALL, Adrian; FARTHING, Christopher Neil; EATHERTON, Andrew John; WO2014/13076; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 330785-84-7, 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.330785-84-7, name is (S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylic acid, molecular formula is C18H21ClN4O4, molecular weight is 392.84, as common compound, the synthetic route is as follows.

In DMF (20 mL) was dissolved (s)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2 -(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidine carboxylic acid (3.9 g, 10 mmol). The solution was cooled in an ice bath. HATU (5.67 g, 15 mmol) and DIPEA (1.93 g, 15 mmol) were added. After 20 min, trans-4-aminocyclohexanol (1.39 g, 12 mmol) was added in batches. The reaction was conducted overnight. LC-MS was used to monitor the reaction. Ethyl acetate (50 mL) and water (50 mL) were added. The separate aqueous phase was washed with ethyl acetate twice. The organic phase was combined, dried, concentrated and purified by silica gel column chromatography (VDCM:VMeOH = 15:1) to give the product (1.5 g, 31 % yield). Molecular formula: C24H32ClN5O4 Molecular weight: 489.21 LC-MS(M/e): 490.11 (M+H+) 1H-NMR (400 MHz, CDCl3): delta 9.63 (1H, s), 8.15 (1H, s), 7.35(1H, s), 7.19 (1H, d), 7.1 (1H, d), 6.26 (1H, s), 4.58 (2H, d), 4.05-4.13 (1H, m), 3.79-3.90 (6H, m), 3.56-3.69 (3H, m), 2.22-2.27 (2 H, m), 1.72-2.17 (8H, m), 1.26-1.45 (4H, m).

Statistics shows that 330785-84-7 is playing an increasingly important role. we look forward to future research findings about (S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylic acid.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); 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. 1013916-37-4, name is 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one, molecular formula is C13H14ClN3O, 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: C13H14ClN3O

Add to dry and clean 2000ml reaction bottle8-cyclopentyl-5-methyl-2-chloro-8H-pyrido[2,3-d]pyrimidinePyridin-7-one (Formula 7) 60g, dissolved in 600g of dichloromethane,Add 90 g of sodium acetate and add 6.0 g of acetic acid.Add 100.0 g of bromine at 0-20 ,After the addition is completed,Stirring reaction for 5 hours,After TLC monitors the reaction of the raw materials,An aqueous solution of 15% sodium hydrogen sulfite in an amount of 800 g was added dropwise.Until the reddish brown bromine was completely destroyed,Stir, dispense,The organic layer is washed twice with water.Wash once again with saturated brine.Distilled under reduced pressure until no flow,Beating with ethanol-water (300g 300g) for 2h,Filtering,The target compound was obtained 65.7g,The yield is 84.28%.The purity of 99.5% of the compound of formula 9 is 0.07%.The compound of formula 10 is present in an amount of 0.01%.

With the rapid development of chemical substances, we look forward to future research findings about 1013916-37-4.

Reference:
Patent; Guang’an Kaite Pharmaceutical Co., Ltd.; Zhang Yaochun; Zhou Fuwei; Liu Xinjun; Zuo Xiaoyong; Zhou Xudong; (11 pag.)CN109320511; (2019); A;,
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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. 139756-21-1, name is 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one. A new synthetic method of this compound is introduced below., COA of Formula: C17H20N4O2

EXAMPLE 21 5-(5-Bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one Bromine (0.93 g, 0.0058 mol) was added dropwise to a stirred solution of 5-(2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one (Preparation 7, 1.1 g, 0.00352 mol) in glacial acetic acid (20 ml). The mixture was stirred at 100 C. for 6.5 hours and the solvent was then removed by evaporation under vacuum. The residue was dissolved in a 9:1 mixture of methanol in dichloromethane (50 ml), and the solution washed with saturated aqueous sodium bicarbonate solution (50 ml), water (50 ml) and saturated brine (50 ml), then dried (MgSO4) and evaported under vacuum. The residue was chromatographed in silica gel (15 g) eluding with a mixture of methanol and dichloromethane (1:99) to give, after crystallisation from acetonitrile, the title compound (0.62 g, 45%), m.p. 157-159 C. Found C,52,41; H,5.25; N,14.01. C17 H19 BrN4 O2 requires C,52.18; H,4.89; N,14.32%.

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, 139756-21-1, 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one.

Reference:
Patent; Pfizer Inc.; US5272147; (1993); A;,
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Pyrimidine – Wikipedia

Electric Literature of 1202759-91-8, 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. 1202759-91-8, name is N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine. A new synthetic method of this compound is introduced below.

Into a 25 ml, three neck flask under nitrogen atmosphere, a solution of N4-(3-aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine (0.15 g) in DMF (5 mL) was charged potassium 3-ethoxy-3-oxopropanoate (0.089 g), EDCI.HCl (0.117 g), HOBt (0.093 g) and TEA (0.164 g). The reaction mixture was stirred for 8 hr at room temperature. Completion of the reaction was monitored by TLC using hexane:ethyl acetate (5:5) as the mobile phase. After completion, the reaction mixture was poured into water. The product was extracted with ethyl acetate and the organic layer was washed with brine. The solvent was removed under reduced pressure at 40 C. The obtained solid was purified by triturating with diethyl ether (2×10 mL) to give 0.19 g of ethyl 3-((3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)amino)-3-oxopropanoate. 1H NMR: DMSO-d6 (400 MHz): 1.182-1.234 (q, 3H, J=6.8), 3.306 (s, 3H), 3.461 (s, 2H), 3.623-3.646 (t, 2H, J=4.8), 4.010-4.033 (t, 2H, J=4.4), 4.090-4.144 (t, 2H, J=7.2), 6.775-6.797 (d, 2H, J=8.8), 7.267-7.283 (d, 2H, J=6.4), 7.511-7.533 (d, 1H, J=8), 7.575-7.591 (d, 1H, J=6.4), 7.817 (s, 1H), 8.058-8.066 (d, 1H, J=3.2), 8.963 (s, 1H), 9.375 (s, 1H), 10.162 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1202759-91-8, its application will become more common.

Reference:
Patent; Celgene Avilomics Research, Inc.; Tester, Richland; Chaturvedi, Prasoon; Zhu, Zhendong; Surapaneni, Sekhar S.; Beebe, Lisa; US2014/179720; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 304693-66-1, 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 304693-66-1, name is 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 17 1-[2-(Trifluoromethyl)pyrimidin-5-yl]ethanol Dissolve 2-(trifluoromethyl)pyrimidine-5-carbaldehyde (11.31 mmol, 1.992 g) in THF (56.56 mL), cool to 0 C., and slowly add methylmagnesium bromide (3 M in Et2O) (33.94 mmol, 11.31 mL). Allow the reaction to warm to room temperature and stir for 2.5 hours. Quench the reaction with 1 N HCl. Add EtOAc and wash with 1 N HCl. Dry the organics over sodium sulfate, filter, and concentrate under reduced pressure to give the title compound (1.663 g, 76.5%). Mass spectrum (m/z): 193.0 (M+H).

According to the analysis of related databases, 304693-66-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; Morphy, John Richard; (15 pag.)US2017/66781; (2017); 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. 56844-38-3, name is 2,4-Dichloro-5-methylthieno[2,3-d]pyrimidine, molecular formula is C7H4Cl2N2S, 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: C7H4Cl2N2S

EXAMPLE 13 Following the procedure of Example 1, the reaction of 3-chloro-4-methoxybenzylamine with 2,4-dichloro-5-methyl-thieno-[2,3-d]-pyrimidine yields 2-chloro-5-methyl-4-(3-chloro-4-methoxybenzylamino)-thieno-[2,3-d]-pyrimidine

With the rapid development of chemical substances, we look forward to future research findings about 56844-38-3.

Reference:
Patent; Cell Pathways, Inc.; US6133271; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 139756-21-1 ,Some common heterocyclic compound, 139756-21-1, molecular formula is C17H20N4O2, 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.

PREPARATION 27 5-(2-Ethoxy-5-nitrophenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one Concentrated nitric acid (0.5 ml) was added dropwise to a stirred solution of 5-(2-ethoxyphenyl)-1-methyl-3-n-propyl-1.6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (2.0 g, 0.0064 mol) in concentrated sulphuric acid (10 ml) at 0 C., and the resulting orange solution was stirred at room temperature for 18 hours. The reaction solution was then added dropwise to stirred ice and water (200 g) and the solid precipitate collected by filtration. This solid was then dissolved in dichloromethane (50 ml) and the solution washed successively with brine (2*30 ml) and water (30 ml), dried (Na2SO4) and evaporated under vacuum to give a yellow solid. Crystallisation from acetonitrile gave the title compound as yellow needles (1.40 g, 61%), m.p. 214-216 C. Found: C,57.35; H,5.21; N,19.49. C17H19N5O4 requires C,57.13; H,5.36; N,19.60%.

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. 139756-21-1, 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cell Pathways, Inc.; US6200980; (2001); B1;,
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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. Formula: C5H5ClN2S

5-methoxy-1H-indazole (500 mg, 3.38 mmol) was dissolved in DMF (10 mL). NaH (148 mg, 3.72 mmol) was added at 0 C, and then 4-chloro-2-(methylthio)pyrimidine (542 mg, 3.38 mmol) was added. After stirring at this temperature for 2 hours, 30 mL of water was added. The reaction solution was filtered, extracted and dried to obtain 5-methoxy-1-(2-(methylthio)pyrimidin-4-yl)-1H-indazole (850 mg, 92%) as a white solid.

The synthetic route of 49844-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hansoh Biomedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; WEI, Mingsong; SUN, Guangjun; TAN, Songliang; GAO, Peng; WANG, Shaobao; XIU, Wenhua; ZHANG, Fujun; BAO, Rudi; (183 pag.)EP3205650; (2017); A1;,
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Application of 5305-40-8 , The common heterocyclic compound, 5305-40-8, name is 4,6-Dichloropyrimidine-5-carbaldehyde, molecular formula is C5H2Cl2N2O, 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.

To the solution of 4,6-dichloropyrimidine-5-carbaldehyde(1.0 g, 0.006 mol) in methanol (20 mL) at -65 C, triethylamine (0.97 mL,1.2 equivalents (eq.)) wasadded. A solution of hydrazine monohydrate (0.274 mL 1.0 eq.) in methanol (10 mL) was slowlydripped into above stirred solution by using a constant-pressure dropping funnel. The mixture wasallowed to warm to room temperature and stirred for 2-3 h. The reaction mixture was concentratedin vacuo and crude product was diluted with water (20 mL), and extracted with EtOAc (60 mL x 3).The combined organic layer was washed with saturated solution of NaCl (60 mL x 3), dried overMgSO4 and concentrated to give compound 2. Yield: 68.9%. 1H-NMR (400 MHz, deuteriated dimethylsulfoxide (DMSO-d6)) delta 14.51 (s, 1H), 8.84 (s, 1H), 8.45 (s, 1H). ESI-MS m/z: 153.00 [M – H]-.

The synthetic route of 5305-40-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fu, Yu; Wang, Yuanyuan; Wan, Shanhe; Li, Zhonghuang; Wang, Guangfa; Zhang, Jiajie; Wu, Xiaoyun; Molecules; vol. 22; 4; (2017);,
Pyrimidine | C4H4N2 – PubChem,
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