Pyrimidines

Synthetic Route of 1193-24-4, 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. 1193-24-4, name is 4,6-Dihydroxypyrimidine. A new synthetic method of this compound is introduced below.

4,6-Dichloro-5-pyrimidinecarbaldehyde; A mixture of DMF (64 mL) and POCl3 (200 mL) at 0 C. was stirred for 1 h and then treated with 4,6-pyrimidinediol (50.0 g, 446 mmol), and further stirred for 0.5 h at rt. Then the heterogeneous mixture was heated under reflux for 3 h. The volatiles were removed under reduced pressure, and the residue was poured into ice water and extracted six times with diethyl ether. The organic phase was washed with aqueous NaHCO3 and water, dried over Na2SO4, concentrated under reduced pressure, and crystallized (EtOAc-petroleum ether) to give 4,6-dichloro-5-pyrimidinecarbaldehyde (43.5 g, 55%); LC-MS (ESI) m/z 177 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1193-24-4, 4,6-Dihydroxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; US2011/152296; (2011); A1;,
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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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H3ClN4

Compound 2 (1.88 g, 0.012 mol)was dissolved in EtOAc (50 mL) and heated to 50 C. After 10 min pyridinium 4-toluenesulfonate(PPTs) (50 mg) were added, followed by the addition of 3,4-dihydro-2H-pyran. The resulting reactionmixture was at stirred 50 C. After the reaction was complete according to the TLC detection, themixture was cooled to room temperature, washed with water (60 mL x 1), and a saturated solution ofNaCl (50 mL x 2), and dried over MgSO4. The ethyl acetate was removed and petroleum ether (60 mL x 2) was added. The mixture was heated and filtered through cotton. Removal of petroleum ether invacuo gives compound 3 as light yellow colored solid. Yield: 76.5%. 1H-NMR (400 MHz, DMSO-d6) delta 8.92 (s, 1H), 8.55 (s, 1H), 6.02 (dd, J = 10.4, 2.4 Hz, 1H), 3.97 (d, J = 12.0 Hz, 1H), 3.76-3.70 (m, 1H),2.49-2.42 (m, 1H), 2.07-2.08 (m, 1H), 1.98-1.94 (m, 1H), 1.85-1.73 (m, 1H), 1.64-1.58 (m, 2H). ESI-MSm/z: 239.06 [M + H]+.

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, 5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Article; Fu, Yu; Wang, Yuanyuan; Wan, Shanhe; Li, Zhonghuang; Wang, Guangfa; Zhang, Jiajie; Wu, Xiaoyun; Molecules; vol. 22; 4; (2017);,
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Electric Literature of 18740-39-1 ,Some common heterocyclic compound, 18740-39-1, molecular formula is C6H2Cl2N2S, 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.

CompoundII-24 (20.51g, 0.1mol, 1.0eq.), Acetic acid (34.3mL, 0.6mol, 6.0eq.) Andmethanol(150mL) placed in a reaction flask was added portionwise at 25 to zinc dust (26.16g, 0.4mol, 4.0eq.), The addition was completed temperaturewas raised to 70 For 3hours, TLC the reaction was complete. Cooling, filtration and the filter cakewas washed twice with methanol, and the filtrate sand column chromatography toobtain compoundI-24 was 10.79g,63.23% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18740-39-1, its application will become more common.

Reference:
Patent; Zhu, Xingyong; Shi, Qingming; Fu, Xiaodong; Sun, Zhangyong; Li, Hui; Jie, Yuanping; (18 pag.)CN105859726; (2016); 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 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4,6-Dichloro-5-methylpyrimidine

To a solution of 2-[2-fluoro-4-[[4-(trifluoromethyl)-2-pyridyl]oxy]phenyl]ethanamine hydrochloride (378 mg, 1 mmol) in N-methyl-2-pyrrolidone (5 mL) was added diisopropylethylamine (0.4 mL, 2.3 mmol). The solution was stirred for 5 min at room temperature at which time 4,6-dichloro-5- methylpyrimidine (150 mg, 0.8 mmol) was added. The reaction mixture was stirred at 80C overnight then allowed to cool to room temperature. Water was added and was extracted with MTBE (3x). The combined organic layers were washed with water, dried over Na2S04, and concentrated in vacuo. The residue was purified by flash silica column chromatography to provide 330 mg (0.80 mmol, 84%) of the light yellow solid product.

With the rapid development of chemical substances, we look forward to future research findings about 4316-97-6.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; GRAMMENOS, Wassilios; CRAIG, Ian Robert; BOUDET, Nadege; MUeLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica May Wilson; LOHMANN, Jan Klaas; MONTAG, Jurith; WO2013/113863; (2013); A1;,
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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. 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, the common compound, a new synthetic route is introduced below. Recommanded Product: 5604-46-6

A mixture of 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (A-1) (9.6 g, 50 mmol), THF (150 mL), and water (50 mL) at 50 C was treated with a solution of hydrazine hydrate (5.1 mL, 100 mmol) in water (50 mL) at room temperature while stirring under nitrogen. Ten mins after addition, the reaction mixture was poured into ice-cold water (250 mL). The THF was evaporated and the remaining aqueous suspension was filtered to give 4-chloro-lH-pyrazolo[3,4-d]pyrimidin-6-amine (A-2) (7.86 g, 93% yield). A small portion was recrystallized from DMF/ water. 1H NMR (500 MHz, DMSO) delta ppm 7.15 (s, 2H), 7.95 (s, 1H), 13.25 (s, 1H). MS (M+l): 170, 172 (1 CI).

The synthetic route of 5604-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TING, Pauline, C.; MA, Shuguang; BLUMENKRANTZ, Neil; CHOWDBURY, Swapan; NEUSTADT, Bernard, R.; WO2012/135084; (2012); A1;,
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Application of 4595-61-3, 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 4595-61-3 as follows.

The titled compound was prepared according to the procedure of Method D using 3,4-difluoro-N’-hydroxybenzimidamide (Tyger) and pyrimidine-5-carbonyl chloride. The pyrimidine-5-carbonyl chloride was prepared by the reaction of pyrimidine-5-carboxylic acid (Maybridge, 138 mg, 1.0 mmol) with oxalyl chloride (Aldrich, 2 M, in CH2Cl2, 1.0 mL, 2.0 mmol) and a drop of dimethylformamide at room temperature over 1 hour with subsequent removal of volatiles under reduced pressure. 1H NMR (300 MHz, DMSO-J6) delta 7.72 (dt, J=10.5, 8.5 Hz, 1 H), 7.94 – 8.05 (m, 1 H), 8.11 (ddd, J=10.9, 7.7, 2.0 Hz, 1 H), 8.12 (none, 1 H), 9.51 (s, 1 H), 9.54 (s, 2 H) ppm; MS (DCIZNH3) m/z 261 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-61-3, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/148452; (2009); A1;,
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Related Products of 7627-44-3, 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. 7627-44-3, name is 2,4-Dichloro-5-(iodomethyl)pyrimidine, molecular formula is C5H3Cl2IN2, 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.

Example 12b. (R)-2-chloro-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][l,4]oxazepineA solution of 2,4-dichloro-5-(iodomethyl)pyrimidine (1.428 g, 4.94 mmol) in THF (2 mL) was cooled to -78°C. (R)-2-amino-l-phenylethanol (0.616 g, 4.49 mmol) in THF (2 mL) was added dropwise. The reaction mixture was stirred at -78°C for 10 minutes. The reaction mixture was cooled in an ice water bath and sodium hydride (60percent dispensed in mineral oil, 0.216 g, 8.99 mmol) was added. After 10 minutes, 2 eq of sodium hydride (60percent dispensed in mineral oil, 0.216 g, 8.99 mmol) were added and the reaction mixture stirred at room temperature for 30 minutes. Water (3 mL) was added and the solvent was evaporated. The residue was partitioned between saturated NaHCObeta (aq) and dichloromethane. The water layer was extracted twice with dichloromethane. The combined organic layers was dried (MgSC^) and concentrated. The crude product was purified by silica flash chromatography using a gradient of methanol (0 to 3percent) in dichloromethane giving 0.193 g of the title compound (16 percent Yield). 1H NMR (500 MHz, DMSO-J6) delta ppm 8.48 (d, 1 H) 7.40 – 7.49 (m, 5 H) 5.60 – 5.67 (m, 1 H) 4.20 (d, 1 H) 3.77 (d, 1 H) 3.20 (br s, 1 H) 3.14 – 3.18 (m, 1 H) 3.04 (br s, 1 H). MS (ES+) m/z 262 [M+H]+.

According to the analysis of related databases, 7627-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; LO-ALFREDSSON, Yvonne; PAULSEN, Kim; RAKOS, Laszlo; ROTTICCI, Didier; WALDMAN, Magnus; WO2010/132015; (2010); A1;,
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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.14080-50-3, name is Thieno[2,3-d]pyrimidin-4(3H)-one, molecular formula is C6H4N2OS, molecular weight is 152.1738, as common compound, the synthetic route is as follows.Product Details of 14080-50-3

EXAMPLE 19 This Example illustrates the preparation of several 4-amino-6-bromo-thieno [2,3-d] pyrimidines according to the invention (Compound Nos. 235-6, 241-2). A mixture of 3,4-dihydrothieno[2,3-d]pyrimidine-4-one (21 g), bromine (30 ml) and acetic acid (300 ml) was stirred at room temperature for three hours, poured into water/ice (1 l) and the 6-bromo derivative filtered off and dried (18.2 g). A portion (17.0 g) was treated with thionyl chloride (230 ml) and N,N-dimethylformamide (3 ml) and refluxed for forty minutes. Excess acid chloride was removed in vacuo and the residue was partitioned between chloroform and water. The organic layer was washed, dried and evaporated to give 6-bromo-4-chlorothieno[2,3-d]pyrimidine (14.7 g). This was treated with a number of amines basically as described in Example 5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14080-50-3, Thieno[2,3-d]pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ICI Australia Limited; US4196207; (1980); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 62968-37-0 ,Some common heterocyclic compound, 62968-37-0, molecular formula is C8H10ClN3O, 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.

General procedure: To a solution of 2-chloroheteroaryl compound 1 (0.50 mmol) in 1,4-dioxane (4.0 mL) were added pinacol boronate 3, 5, or 7 (0.60 mmol), Pd(OAc)2 (1.1 mg, 5.0 mumol), S-Phos (4.1 mg, 10.0 mumol), and 2 M LiOH solution (1.0 mL, 2.0 mmol) at room temperature, and the mixture was stirred for 30 min at 80 C under N2 atmosphere. The reaction was quenched by adding water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by silica-gel column chromatography. The solvent was removed in vacuo, and the residue was triturated with Et2O to give biaryl compounds.

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. 62968-37-0, 4-(2-Chloropyrimidin-4-yl)morpholine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Asano, Shigehiro; Kamioka, Seiji; Isobe, Yoshiaki; Tetrahedron; vol. 68; 1; (2012); p. 272 – 279;,
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Synthetic Route of 13223-25-1, 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 13223-25-1 as follows.

A mixture of (2R*, 4S*) -4-amino-2-ethyl-6-methoxy-3, 4-dihydro-2H- [1, 5] naphthyridine-l-carboxylic acid ethyl ester (300 mg), 2-chloro-4,6- dimethoxypyrimidin (468 mg), N, N-diisopropylethylamine (0.467 ml) and 1,4-dioxane (5 ml) is heated under reflux for 2 days. The reaction solution is concentrated under reduced pressure, and the resulting residue is purified by column chromatography (silica gel; hexane: ethyl acetate = 80 : 20-60 : 40) to give (2R*, 4S*)-4- (4, 6-dimethoxypyrimidin-2-yl) amino-2- ethyl-6-methoxy-3, 4-dihydro-2H- [1, 5] naphthyridine-1-carboxylic acid ethyl ester (280 g). MS (m/z) : 418 [M+H] +

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13223-25-1, its application will become more common.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; WO2005/95395; (2005); A2;,
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