Tag: M.W:200-300

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;,
Pyrimidine | C4H4N2 – PubChem,
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

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
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. 89581-38-4, name is Methyl 5-bromopyrimidine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. name: Methyl 5-bromopyrimidine-2-carboxylate

An solution of NaBH4 (510 mg, 2.70 mmol) in H2O (10 mL) was introduced drop-wise to a solution of methyl 5-bromopyrimidine-2-carboxylate (3.05 g, 14.1 mmol) in THF (100 mL) at 0 C. The mixture was allowed to warm slowly to RT overnight. The majority of the THF was evaporated, and the resulting residue was diluted with EtOAc (200 mL). The organic fraction was washed with brine (200 mL), dried (MgSO4) and purified over silica, eluting with 0-60% EtOAc:n-heptane) to afford i (510 mg, 19%). MS: 189.0 & 191.0; 1:1 [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, 89581-38-4, Methyl 5-bromopyrimidine-2-carboxylate.

Reference:
Patent; Biota Europe Ltd.; Lunniss, Christopher James; Palmer, James T.; Pitt, Gary Robert William; Davies, David; Axford, Lorraine Claire; US2013/252938; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 83410-15-5, name is 4-Chloro-5-iodo-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H4ClIN2

Reference Example 54-Chloro-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine4-Chloro-5-iodo-6-methylpyrimidine and [4-(trifluoromethyl)phenyl]ethynylzinc bromide were reacted in a solvent mixture of tetrahydrofuran and N,N-dimethylformamide (1:1) in the presence of tetrakis(triphenylphosphine)palladium while stirring under room temperature to heating to obtain a target substance. The target substance was subjected to e.g., proton nuclear magnetic resonance spectrometry (1H-NMR) and mass spectrometry (MS) and confirmed as the titled compound. Furthermore, MS measurement result is shown.Mass spectrum: 297,299.

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, 83410-15-5, 4-Chloro-5-iodo-6-methylpyrimidine.

Reference:
Patent; Nishio, Tetsuya; US2011/319618; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3740-92-9, 4,6-Dichloro-2-phenylpyrimidine, 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, Application In Synthesis of 4,6-Dichloro-2-phenylpyrimidine, blongs to pyrimidines compound. Application In Synthesis of 4,6-Dichloro-2-phenylpyrimidine

EXAMPLE 6 This Example illustrates the preparation of (E)-methyl 2-[2-(6-chloro-2-phenylpyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (Compound No.378 of Table II). A stirred solution containing (E)-methyl 2-(2-hydroxyphenyl)-3-methoxypropenoate (208mg) and 4,6-dichloro-2-phenylpyrimidine (225mg, prepared according to the method of D. B. Harden, M. J. Mokrose and L. Strekowski, J.Org.Chem, 1988, 53, 4137-4140) in DMF (5 ml) was cooled to 0° C. Potassium carbonate (138mg) was then added and stirring was continued at 0° C. under an atmosphere of nitrogen. After 3 hours, the temperature was allowed to rise to room temperature and stirring was continued overnight. The reaction mixture was diluted with water and then acidified with dilute hydrochloric acid. The resulting mixture was extracted with ether (*3) and the combined ether extracts were washed successively with dilute aqueous sodium hydroxide solution (*2) and water (*3) and then dried. Evaporation of the solvent gave an oil (0.31 g), which solidified on standing. Chromatography (eluent ether-hexane, 1:2) afforded the title compound (0.12 g, 30percent) as an off-white solid; m.p. 118-120° C.; 1H NMR: delta 3.54(3H,s), 3.67(3H,s), 6.65(1H,s), 7.22-7.50(7H,m), 7.44(1H,s), 8.28-8.33(2H,m) ppm; IR maxima: 1708, 1631 cm-1.

The synthetic route of 3740-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Clough, John Martin; Godfrey, Christopher Richard Ayles; Streeting, Ian Thomas; Cheetham, Rex; de Fraine, Paul John; Bartholomew, David; Eshelby, James John; US2003/60626; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 16097-63-5 ,Some common heterocyclic compound, 16097-63-5, molecular formula is C6H4ClF3N2S, 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 a solution [OF 2-THIOMETHYL-4-CHLORO-6-TRIFLUOROMETHYLPYRIMIDINE] (1.9996 g, 8.75 mmol) in [MEOH] (50 mL) was added morpholine (1.5 mL, 17.2 [MMOL).] The solution was stirred overnight, concentrated in vacuo, and the resulting white solid was collected by vacuum filtration and washed with water. To a solution of the solid in [CH2C12] (50 mL) was added m- chloroperbenzoic acid (4.53 g, 26.3 mmol), and the resulting solution was stirred for 2 h at which time it was observed to be a white suspension. The solvent was removed in vacuo, and then [MEOH] (50 mL) was added followed by hydrazine monohydrate (3.0 mL, 61.8 mmol). The solution was stirred for 16 h, and was then concentrated to about one-half volume in vacuo. Water (100 mL) was then added to the resulting suspension, and the observed white solid was collected by vacuum filtration. This material was then washed with water and dried in vacuo to afford 1.7193 g of the title compound [(75%)] as a white solid. MH+ 264.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16097-63-5, its application will become more common.

Reference:
Patent; Smithkline Beecham corporation; WO2003/101442; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 33097-13-1, 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. 33097-13-1, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below.

[0329] Step 1 : To a suspension of 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (330 mg, 1.5 mmol) in DMF (3 mL) was added m-anisidine (231 mg, 1.875 mmol). After stirring at room temperature for 4 h, the mixture was diluted with water, the resulting precipitate was collected by filtration to give 4-chloro-2-(methythio)-6-(3- (methoxy)phenylamino)pyrimidin-5-carbonitrile (600 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33097-13-1, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; XU, Qing; HUANG, Wolin; JIA, Zhaozhong J.; SONG, Yonghong; WO2012/61415; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 130049-82-0, Adding some certain compound to certain chemical reactions, such as: 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one,molecular formula is C11H15ClN2O2, 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 130049-82-0.

Into a clean 2L, three-necked RB flask equipped with shaft, condenser, and thermo socket was charged 600 ml of DMF, lOOg (0.404 moles) of 3-(2-Chloroethyl)-6,7,8,9- tetrahydro-9-hydroxy-4H-pyrido[l52-a]pyrimidin-4-one of formula- VI obtained from Example 5, 67.19g (0.404 moles) of potassium iodide, 111.91g (0.808moles) of potassium, carbonate and 103.68g (0.404 moles) of 6- fluoro-3-(4- piperidinyl)-l,2- benzisoxazole HCl (formula-VII). The reaction mass was heated to 60-650C and maintained for 18h. Reaction mass was cooled to 25-300C, stirred for Ih and filtered under vacuum. The wet cake was washed with 200ml of DMF. The wet cake was leached with 2 x 500ml of water and 1 x 500ml of methanol. The wet material was dried in the oven at 70-750C for Ih to yield 114g of technical grade paliperidone. Above technical grade paliperidone was recrystallized from methanol via charcoal treatment to get 6Og (34.74% yield) of pure paliperidone. Purity by HPLC is > 99.8%.S Alternatively technical grade paliperidone was purified by the following chemical method.Above technical grade paliperidone (114g) was dissolved in 6.84L of methanol at 65- 7O0C. Charcoal (20 g) was added to the resultant solution and filtered under vacuum using a filter aid. The solvent was distilled of from the filtrate at 60-650C using0 rotavapor under vacuum to get a cream colored solid. Methanol (575 ml) was added to the solid and stirred for 45min at 25-300C. The reaction mass was filtered and dried in an oven at 70-750C to get 90 g of paliperidone.Into a clean and dry IL, three-necked RB flask equipped with shaft, thermo socket,5 addition funnel and stopper was charged 57.0 ml of cone. HCl and 570 ml of water.The reaction mass was stirred for 5min and charged the above solid (9Og). The reaction mass was stirred for 5-10min at 25-300C to get yellow colored clear liquid. pH of the reaction mass was adjusted to 6.0 to 6.5 by dropwise addition of dilute(concentrated aq ammonia solution was diluted with equal volume of water) aq.0 ammonia solution. The reaction mass was stirred for 30min and filtered under vacuum. The wet solid was dried in the oven at 70-750C to get 88g of paliperidoneHCl.Above solid was transferred taken into a IL RB flask containing 570 ml of methanol.5 The suspension was stirred for 30min at 25-3O0C, filtered under vacuum and dried in the oven at 70-750C for Ih to get 85 g pure paliperidone HCl. HPLC purity is > 99.80%.Above paliperidone HCl salt (85.0 g) and 2280 ml of water were suspended in a RB0 flask at 25-300C. pH was adjusted to 8.5 to 9.0 by adding aq. potassium carbonate solution (prepared from 57 g of potassium carbonate and 570 ml of water). The resultant cream-colored suspension was stirred for 30 min at 25-300C and filtered under vacuum. The wet cake was washed with 1500ml of water followed by 300ml of methanol. The wet cake was triturated with 450 ml of methanol for 30 min and filtered. Paliperidone was dried in vacuum oven at 65-70C for 4h to afford 59 g (34.33%) of pure paliperidone. Purity by HPLC is > 99.8%. 1H-NMR (CDCl3): 1.75 (m, 2H, aliphatic-H), 1.95 (m, IH, aliphatic-H), 2.15 (m, 5H, aliphatic-H), 2.24 -2.40 (m, 5H, aliphatic-H), 2.56 (t, 2H, -CH2-, J = 6.84 Hz), 2.76 (t, 2H, -CH2-, J = 7.82 Hz), 3.09 (m, IH, aliphatic-H), 3.18 (d, 2H, aliphatic-H, J =11.72 Hz), 3.92 (m, 2H, aliphatic-H), 4.15 (s, IH, -OH, D2O exchangeable), 4.50 (dd, IH, aliphatic-H J = 3.91 Hz), 7.07 (m, IH, aromatic-H), 7.23 (m, IH aromatic-H), 7.70 (dd, IH, aromatic-H, J= 2.93 Hz).

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. 130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NATCO PHARMA LIMITED; WO2009/10988; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia