Pyrimidines

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. 14080-23-0, name is 2-Cyanopyrimidine, molecular formula is C5H3N3, 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. Computed Properties of C5H3N3

Methyl pyrimidine-2-carboxylate (11):A stirred solution of cyano 10 (1.01 g, 9.52 mmol) in methanolic HC1 (20 mL, 4N solution) was refluxed for 16 h and concentrated under reduced pressure; the residue was diluted with water and neutralized with sodium bicarbonate solution. The aqueous layer was extracted with 20% IPA/CH2CI2, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford ester 11 (0.43 g, 32.5%) as liquid.TLC: 100% EtOAc (Rf: 0.1)1H NMR (500MHz, CDC13): delta 8.96 (d, J = 5.0 Hz, 2H), 7.50 (t, J = 5.0 Hz, 1H), 4.08 (s, 3H). Mass (ESI): 139 (M++l).

With the rapid development of chemical substances, we look forward to future research findings about 14080-23-0.

Reference:
Patent; THERACRINE, INC.; SUN, Lijun; BARSOUM, James; WESTER, Ronald; WO2013/13238; (2013); A2;,
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Application of 153286-94-3, 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 153286-94-3, name is 5-Ethynylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Scheme 6-5: In Step 1 the appropriately substituted indole is acylated as known in the art. In Step 2 the appropriately substituted heterocycle is subjected to a bromide species of the appropriate linker to afford the appropriately protected species. In Step 3 the appropriately substituted aryl bromide is subjected to a terminal alkyne as known in the art to afford an internal alkyne. In Step 4 the appropriately substituted para-methoxybenzyl alcohol is deprotected in the presence of CAN to afford a free alcohol. In Step 5 the appropriately substituted phenol is subjected to a sulfonic anhydride to afford a leaving group. In Step 6 the appropriately substituted aryl species is converted to a boronic acid as known in the art. In Step 7 the appropriately substituted boronic acid is subjected to copper bromide to afford an aryl bromide species. In an alternative embodiment this synthetic protocol can simply be applied to other indole isomers to afford substituents on alternative positions.

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 153286-94-3, 5-Ethynylpyrimidine.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (340 pag.)WO2017/35415; (2017); 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. 35265-83-9, name is 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine, the common compound, a new synthetic route is introduced below. Formula: C7H4Cl2N2S

Reference Example 18 4-Allylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine In DMF was dissolved 1.50 g (6.8 mmol) of 2,4-dichloro-7-methylthieno[3,2-d]pyrimidine, and then 917 mg (16.1 mmol) of allylamine 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=1/8) to give 1.25 g (yield: 76.2%) of the title compound. NMR (delta, CDCl3): 2.43 (3H, s), 4.28-4.33 (2H, m), 5.09 (1H, br), 5.22-5.35 (2H, m), 5.94-6.07 (1H, m), 7.36 (1H, s)

The synthetic route of 35265-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NAKASHIMA, YOSHIHARU; FUJITA, TAKASHI; HIZUKA, MICHIYO; IKAWA, HIROSHI; HIRUMA, TORU; US2001/6969; (2001); A1;,
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Electric Literature of 5424-21-5, 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.5424-21-5, name is 2,4-Dichloro-6-methylpyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.0047, as common compound, the synthetic route is as follows.

A mixture of 2,4-dichloro-6-methyl-pyrimidine (40 g, 245 mmol) in NH3.H2O (500 mL) was stirred at 25 C for 44 h. The crude product was filtered and the resulting solution was concentrated under reduced pressure. The remaining residue was purified by silica gel chromatography to afford 2-chloro-6-methyl-pyrimidin-4-amine (10.4 g, 72.4 mmol, 30% yield) as a white solid. LCMS (ESI): m/z: [M +H] calculated for C5H7QN3 : 144.0; found 144.3.

The chemical industry reduces the impact on the environment during synthesis 5424-21-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; REVOLUTION MEDICINES, INC.; KOLTUN, Elena S.; AAY, Naing N.; BUCKL, Andreas; MELLEM, Kevin T.; BLANK, Brian R.; PITZEN, Jennifer; WANG, Gang; JOGALEKAR, Ashutosh S.; WON, Walter S.; TZITZILONIS, Christos; LI, Jie Jack; GILL, Adrian Liam; CREGG, James Joseph; (207 pag.)WO2019/118909; (2019); A1;,
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Electric Literature of 6693-08-9, 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. 6693-08-9, name is 2,4,6-Trichloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below.

2,4,6-trichloro-5-fluoropyrimidine (1.54 g, 7.65 mmol),(2S,3S)-3-Aminobicyclo[2.2.2]octane-2-carboxylic acid ethyl ester hydrochloride (1.79 g, 7.65 mmol)And K2CO3 (2.64 g, 19.12 mmol) was suspended in DMF (15 mL).The resulting mixture was stirred at room temperature overnight.The reaction solution was quenched by adding H 2 O (50 mL).Extract with ethyl acetate (50 mL × 3),The combined organic phases were washed with saturated brine (100 mL×3).Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate.The residue was purified by silica gel column chromatography (EtOAc /EtOAcThe title compound was obtained as a pale yellow solid(0.69g, 25%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6693-08-9, 2,4,6-Trichloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; (138 pag.)CN108276401; (2018); A;,
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Reference of 274693-26-4, 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. 274693-26-4, name is 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol. A new synthetic method of this compound is introduced below.

(1) cooling the toluene solution of the upper step product remaining in the 200L reaction vessel to 10 to 20 C;(2) adding 37.062 kg of hydrochloric acid and 55 L of methanol mixed solution cooled to 10 to 20 C into the reaction kettle under stirring;After the addition is completed, the mixture is kept at 10 to 20 C for 3 to 4 hours;(3) TLC detection reaction was completed, ethyl acetate: isooctane = 1:1, and the upper organic phase plate was taken;Stop stirring, let stand for stratification, and separate the lower methanol water phase for use;(4) adding a lower methanol aqueous phase separated in the above step to a 500 L reaction kettle, and adding 20% potassium carbonate aqueous solution (25.406 kg of potassium carbonate and 101.64 L of purified water) under stirring;Finally adjust the pH between 7-9;(5) adding 55 L of ethyl acetate under stirring, and stirring for 30 min;Stop stirring, let stand layering, separate the lower layer of water, and transfer the upper organic phase to the PE barrel for use;(6) The lower aqueous phase was transferred to the reaction vessel, 55 L of ethyl acetate was added, and the mixture was stirred for 30 minutes; the stirring was stopped, the layer was allowed to stand, and the lower aqueous phase was separated; (7) Combine the two organic phases, add 200L reaction kettle, add 55L purified water under stirring, and stir for 30 minutes;Stop stirring, let stand for stratification, and separate the lower aqueous phase;Then, 55 L of purified water was added to the reaction vessel, and the mixture was stirred for 30 minutes; the stirring was stopped, the layer was allowed to stand, and the lower aqueous phase was separated;(8) adding 686 g of activated carbon to the organic phase (the amount of activated carbon is 5% of the crude product, the crude product is calculated in 100% yield), heating to 40-50 C, stirring for 30 minutes;(9) Filter the filter pad with diatomaceous earth (about 100 g of diatomaceous earth), distill off the solvent under reduced pressure at 50 C, and steam until no more liquid flows out;Then add 11 L of ethyl acetate to distill off the solvent, repeat 2 times until the solid is produced, no more liquid will flow out;To the residue, 68.61 L of ethyl acetate was added and heated to 50-60 C to dissolve (the amount of ethyl acetate was 5 times the mass of the crude product, and the crude product was calculated in 100% yield);Transfer the solution to a 50L reactor and heat to 50-60 C; (10) adding 82.33 L of isooctane preheated to 50-60 C under stirring (the amount of isooctane is 1.2 times the volume of ethyl acetate);Control the addition speed to keep the internal temperature above 50 C, and gradually precipitate solids during the addition;(11) After the addition is completed, the temperature is lowered by stirring to a temperature of 20 to 30 C, and stirred for 1 hour;(12) further cooling to 0 to 10 C and stirring for 2 hours;(13) centrifugal filtration, the reaction kettle and the filter cake are washed with a mixture of 13.72 L of ethyl acetate and 16.47 L of isooctane precooled to 0 to 10 C;(14) The filter cake was dried under vacuum at 45 to 55 C for 8 to 12 hours to obtain 11.6 kg of ticagrelor crude product (Im-4); the yield was 85%. (1) Add 45 L of dichloromethane and 108 L of t-butanol to a 200 L crystallizer; add 11.5 kg of ticagrelor crude by stirring. (2) heating to 50 ~ 60 C under stirring for 1 hour; cooling to 20 ~ 30 C, stirring for 1 hour;(3) further cooling to 0 to 10 C for 2 hours;(4) centrifugal filtration, the reaction kettle and the filter cake are rinsed with water precooled to 0 to 10 C;(5) The filter cake was dried under vacuum at 45-55 C for 8 to 12 hours to obtain 10.7 kg of ticagrelor; the weight yield was 93%. After testing total impurities of 0.74%, SM1: 0.09%, Im-1: 0.08%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,274693-26-4, its application will become more common.

Reference:
Patent; Beijing Dongxuli Pharmaceutical Technology Co., Ltd.; Bao Yiwen; Wang Yajun; (20 pag.)CN108329320; (2018); A;,
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Related Products of 54-20-6, 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. 54-20-6, name is 5-(Trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, molecular formula is C5H3F3N2O2, 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.

5-trifluoromethyluracil (48.0 g, 267 mmol) is suspended in 210 mL phosphorus oxychloride (POCI3) while moisture is excluded. Diethylaniline (47.7 g, 320 mmol) is slowly added dropwise to this suspension such that the temperature remains between 250C and 300C. After the addition has ended the mixture is stirred for a further 5 – 10 min in the water bath and the mixture is heated for 5- 6 h with the exclusion of moisture at 80 – 900C. The excess POCI3 is destroyed by stirring into approx. 1200 g of sulphuric acid mixed with ice water and the aqueous phase is immediately extracted 3 x with in each case 500 mL diethyl ether or te/t.-butylmethyl ether. The combined ethereal extracts are washed 2 x with 300 mL sulphuric acid mixed with ice water (approx. 0.1 M) and with cold saline solution and immediately dried on sodium sulphate. The desiccant is filtered off and the solvent is eliminated in vacuo. The residue is distilled in vacuo (10 mbar) through a short column (20 cm) (head temperature: 65 – 700C), to obtain a colourless liquid that is bottled and stored under argon. TLC: Rf = 0.83 (chex:EE = 3:1)

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 54-20-6, 5-(Trifluoromethyl)pyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; SAPOUNTZIS, Ioannis; BETZEMEIER, Bodo; STADTMUELLER, Heinz; WO2010/55117; (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.635698-56-5, name is tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, molecular formula is C12H15Cl2N3O2, molecular weight is 304.17, as common compound, the synthetic route is as follows.Formula: C12H15Cl2N3O2

To the mixture of tert-butyl 2,4-dichloro-7, 8-dihydropyrido[4,3 -d]pyrimidine6(5H)-carboxylate (4.00 g, 13.15 mmol) in CH2C12 (15.00 mL) was added HC1/dioxane (4 N,15.00 mL). The mixture was stirred at 15 C for 15 h. LCMS showed one main peak of desired product and about 5% of starting material. The mixture was stirred at 30 C for 1 h. LCMS showed desired product was major. The mixture was concentrated under reduced pressure to afford the title compound (3.07 g, crude, HC1 salt) as a white solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,635698-56-5, tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (2016); A1;,
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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. 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4HCl2FN2

To a mixture of sodium (450 mg, 19 mmol) in methanol (20 mL) was added a solution of 2,4-dichloro-5-fluoropyrimidine (3.25 g, 19 mmol) in methanol (10ml_). The reaction mixture was stirred at room temperature overnight before being partitioned between water and diethyl ether. The organic phase was separated, washed with brine and evaporated to dryness to give the title compound as an orange oil (80%), which was used in the next step without further purification.1H-NMR delta (400 MHz, CDCI3): 4.1 (s, 3H), 8.2 (s, 1 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, 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; ALMIRALL, S.A.; BACH TA?A, Jordi; PAGES SANTACANA, Lluis, Miquel; TALTAVULL MOLL, Joan; EASTWOOD, Paul, Robert; GONZALEZ RODRIGUES, Jacob; GIULIO MATASSA, Victor; WO2011/101161; (2011); A1;,
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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 14001-61-7, name is 2-Methoxy-4,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Methoxy-4,6-dimethylpyrimidine

General procedure: Preparation of 1a’-3f’ and 1g-5g. A mixture of pyrimidines (2.00 mmol) and benzaldehydes (4.00 mmol) in 5 N NaOH solution (20 mL) containing tetrabutylammonium hydrogen sulfate (0.10 g, 0.29 mmol) was refluxed. After cooling, the precipitates were filtered off. The products were purified by recrystallization from EtOAc. Otherwise, the mixture was extracted with CH2Cl2. Then, the organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography to give the products.

With the rapid development of chemical substances, we look forward to future research findings about 14001-61-7.

Reference:
Article; Lee, Yun Suk; Kim, Hye Yun; Kim, Youngsoo; Seo, Jae Hong; Roh, Eun Joo; Han, Hogyu; Shin, Kye Jung; Bioorganic and Medicinal Chemistry; vol. 20; 16; (2012); p. 4921 – 4935;,
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