Tag: M.W:100-200

Application of 3680-69-1 ,Some common heterocyclic compound, 3680-69-1, molecular formula is C6H4ClN3, 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 4-chloro-7H-pyrrolo[2,3-d] pyrimidine (15.4 g,0.100 mol) in tetrahydrofuran, 60% sodium hydride (8.0 g, 0.200 mol)was added in batches under ice bath. The reaction mixture was stirredunder ice bath for 0.5 h, and then chloromethyl pivalate (30.1 g,0.200 mol) was added to the mixture. Subsequently, the reaction wasstirred at room temperature for 1.5 h. After completed, the mixture waspoured into saturated ammonium chloride solution. The mixture wasextracted with ethyl acetate (50 ml×5), the organic layer was washedwith brine, dried over anhydrous Na2SO4, and then filtered and concentratedto yield 4 as a yellow solid (27.5 g, 85.0%). MS (ESI) m/z:268.4 [M+H]+

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. 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jiang, Feng; Zang, Linghe; Miao, Xiuqi; Jia, Fang; Wang, Jie; Zhu, Minglin; Gong, Ping; Jiang, Nan; Zhai, Xin; Bioorganic and Medicinal Chemistry; vol. 27; 18; (2019); p. 4089 – 4100;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3934-20-1, Adding some certain compound to certain chemical reactions, such as: 3934-20-1, name is 2,4-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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 3934-20-1.

Example 2 Preparation of Intermediate 4-(4-chloro-pyrimidin-2-yl)-piperazine-1-carboxylic Acid Tert-Butyl Ester (I-2a): To a suspension of 2,4-dichloropyrimidine (1.00 g, 6.71 mmol) in 13.4 mL of toluene was added 4-methyl-piperazine-1-carboxylic acid tert-butyl ester (1.34 g, 6.71 mmol). The reaction was heated to reflux overnight, then cooled to room temperature and concentrated in vacuo. The residue was taken up in 20 mL of water and extracted with ethyl acetate (2*40 mL). The combined organic layers were washed with brine (25 mL), then dried over sodium sulfate, filtered, and concentrated in vacuo to an off-white solid. Flash column chromatography (silica gel, gradient elution from 5% ethyl acetate-hexanes to 20% ethyl acetate-hexanes) yielded 1.14 g of the title compound (I-2a). 1H NMR (400 MHz, CDCl3) delta 8.15 (d, 1H); 6.52 (d, 1H); 3.80 (m, 4H); 3.48 (m, 4H); 1.47 (s, 9H). MS (APCI+) Calc: 298, Found: 299.1 (M+1).

According to the analysis of related databases, 3934-20-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chiang, Phoebe; Novomisle, William A.; Welch JR., Willard M.; US2003/105106; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3764-01-0, 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 3764-01-0, name is 2,4,6-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

The 4-chloro-2-(2-difluoromethylbenzimidazol-l-yl)-6-mophiholinopyrimidine used as a starting material was prepared as follows :-; Diisopropylethylamine (6.3 g) was added to a stirred solution of 2,4,6-trichloropyrimidine (10 g) in methylene chloride (100 ml) that had been cooled to 0°C. Morpholine (4.3 g) was added slowly and the resultant reaction mixture was stirred at ambient temperature for 3 hours. The mixture was washed with a saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using an increasingly polar solvent gradient from mixtures of isohexane and methylene chloride. The more polar isomeric product was collected. There was thus obtained 2,4-dichloro- 6-morpholinopyrimidine as a solid (7.8 g); NMR Spectrum: (DMSOd6) 3.60-3.74 (m, 8H), 6.96 (s, IH); Mass Spectrum: M+H+ 234.

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32072; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 51-20-7, 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. 51-20-7, name is 5-Bromouracil. A new synthetic method of this compound is introduced below.

General procedure: Nitrogenous compounds (1eq. each) viz. thymine (for 2), 5-bromouracil (for 3), adenine (for 4), were first dissolved in warm DMSO. To this solution TEA and a solution of [6]-shogaol (1eq.) in DMSO was added. Reaction mixture was stirred at room temperature for 24h. The crude product was extracted using ethyl acetate (3×50mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to get crude product as a syrupy residue which was further purified by flash chromatography to afford the corresponding pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51-20-7, 5-Bromouracil, and friends who are interested can also refer to it.

Reference:
Article; Singh, Vinay Kr; Doharey, Pawan K.; Kumar, Vikash; Saxena; Siddiqi; Rathaur, Sushma; Narender, Tadigoppula; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 74 – 82;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3934-20-1, Adding some certain compound to certain chemical reactions, such as: 3934-20-1, name is 2,4-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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 3934-20-1.

Under nitrogen, 100mL three-mouthed flask successively add 002-2 (1.3g, 8.73mmol), 13mL DME, FeCl3 (1.414g, 8.72mmol) and 001-5 (974mg, 7.43mmol). In an oil bath at 64 deg.C react overnight. After completion of the reaction, the reaction mixture was down to room temperature, filtered, the filter cake washed 3 times with 20mL of methanol, the organic phases were combined and concentrated to dryness, and driedto give 1.0g 005-1 (47%), as a yellow solid.

According to the analysis of related databases, 3934-20-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Shaletech Technology Co., Ltd; Jiang, Yueheng; (28 pag.)CN105237515; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 58347-49-2, 7-Chloropyrazolo[1,5-a]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, Safety of 7-Chloropyrazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Safety of 7-Chloropyrazolo[1,5-a]pyrimidine

EXAMPLE 18N-r(35r)-l-{7-Fluoro-8-methyl-3-r(15r)-l-(pyrazolorL5-alphalpyrimidin-7-ylamino>;)ethyl1- quinolin-2-vUpyrrolidin-3-yl]cyclopropanecarboxamide(5)-(-)-3 -Amino- 1-pyrrolidinecarboxylic acid tert-butyl ester (500 mg, 2.68 mmol), DCM (30 mL), DIPEA (2 mL) and cyclopropanecarbonyl chloride (0.275 mL, 3 mmol) were combined at r.t. under a nitrogen atmosphere. The reaction mixture was stirred for 1 day, then diluted with DCM (50 mL) and washed with water (50 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to give a brown oil. This oil, MeOH (10 mL) and 2N HCl in Et2O (5 mL) were stirred at r.t. for 3 days. The reaction mixture was then concentrated in vacuo. The resulting material, Intermediate 15 (500 mg, 1.48 mmol), H-BuOH (16 mL) and DIPEA (2 mL) were combined in a sealed tube and heated to 13O0C for 15 days. The reaction mixture was cooled, concentrated onto silica and purified by column chromatography (SiO2, 0-100% EtOAc in isohexane) to give a tan solid. This material, MeOH (10 mL) and 2N HCl in Et2O (7 mL) were combined and stirred at r.t. for 24 h. The reaction mixture was concentrated to give a brown glass. A portion of this material (50 mg, 0.127 mmol), n- BuOH (6 mL), DIPEA (1 mL) and 7-chloropyrazolo[l,5-alpha]pyrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated under microwave irradiation to 16O0C for 2 h. The reaction mixture was then concentrated to dryness and purified by preparative HPLC to give the title compound (32.3 mg, 54%) as a brown glass. 6H (DMSO-d6) 8.44 (IH, d, J6.91 Hz), 8.38 (IH, d, J6.91 Hz), 8.25 (IH, s), 8.17 (IH, d, J 2.27 Hz), 8.10 (IH, d, J5.21 Hz), 7.57 (IH, dd, J8.84, 6.41 Hz), 7.10 (IH, t, J9.10 Hz), 6.49 (IH, d, J2.27 Hz), 6.06 (IH, d, J 5.28 Hz), 5.27 (IH, m), 4.50-4.42 (IH, m), 4.07- 3.94 (2H, m), 3.82-3.74 (IH, m), 3.60 (IH, dd, J 10.47, 5.21 Hz), 2.51 (3H, s), 2.32-2.23 (IH, m), 2.04-1.94 (IH, m), 1.77 (3H, d, J6.54 Hz), 1.66-1.58 (IH, m), 0.77-0.67 (4H, m). LCMS (ES+) 474 (M+H)+, RT 2.51 minutes {Method I).

The synthetic route of 58347-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products 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.

EXAMPLE 2 4,6-Dihydroxypyrimidine (20.5 g) was dispersed with agitation in dichloromethane (400 ml). Dimethylaniline (40.4 g) was added to the agitated mixture and the system was sealed (except for a vent line to a scrubber). Phosgene gas (56 g) was introduced from a cylinder and condensed onto a cold finger and collected in a pressure equalised dropping funnel. Once collected, the phosgene liquid was added to the reaction mixture over 15 minutes. The mixture was heated and agitated at reflux (29 C. approximately) for 17 hours after which time the mixture was cooled to room temperature and the excess phosgene removed by sparging with nitrogen. Water (400 ml) was added slowly to the agitated reaction mass with cooling to maintain the temperature at ambient. The organic layer was separated, and the aqueous was then extracted with dichloromethane (2*100 ml). The combined extracts were dried over anhydrous sodium sulphate and concentrated by rotary evaporation to give 4,6-dichloropyrimidine as an orange crystalline solid (27 g), equivalent to a yield of 80% (hplc analysis).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-24-4, its application will become more common.

Reference:
Patent; Zeneca Limited; US5750694; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 54326-16-8 , The common heterocyclic compound, 54326-16-8, name is 5-Chloropyrimidin-2(1H)-one, molecular formula is C4H3ClN2O, 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.

EXAMPLE 25 5-Chloro-1-(4-cyanophenacyl)pyrimidin-2-one A suspension of 5-chloropyrimidin-2-one (412 mg) and 2-bromo-4′-cyanoacetophenone (677 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for one hour. Water (100 ml) was added and the collected solid was crystallized from ethyl acetate to give the title pyrimidinone (375 mg,); m.p. 236-240; lambdamaxEtOH 248 nm (epsilon 26140), 289 nm (epsilon 2130), lambdainf 254 (epsilon 22800).

The synthetic route of 54326-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; US4636509; (1987); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1, 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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, 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.

Into a round bottom flask the catalyst PdCl2(dppf), under an atmosphere of nitrogen, was placed with 15 mL of toluene along with a stir bar. A suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 1.47 g, 9.57 mmol) in 15 mL of toluene was added at room temperature. After stirring for 10 minutes, methylmagnesium bromide (17.00 mL, 3.00 M in ether, 51.00 mmol) was added dropwise. The solution turned from orange to yellow, and was slowly heated to 60 C. and stirred for 3 hrs at 60 C. and then overnight at room temperature. The resulting dark orange reaction mixture was quenched with 1 N hydrochloric acid and adjusted to pH~5, then extracted with ethyl acetate and water saturated with sodium chloride. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluding with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a yellow solid (42, 202 mg). 1H-NMR(dmso-d6) was consistent with the desired compound. MS(ESI) [M+H+]+=134.3.

According to the analysis of related databases, 3680-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Plexxikon, Inc.; US2009/286783; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1194-78-1, 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 1194-78-1 as follows.

(D) 7-Chloro-1H-1,2,3-triazolo[4,5-d]pyrimidin-5-amine A solution of 6-chloro-2,4,5-pyrimidinetriamine (10.94 g, 0.0686 mol) and isoamyl nitrite (9.20 ml, 0.0686 mol)in dioxane (500 ml, freshly purified by passage through basic alumina) was heated under nitrogen with stirring for 2 hours at 90. The reaction mixture was cooled, treated with activated carbon, filtered, and concentrated to 150 ml. Petroleum ether (250 ml, bp 35-60) was added. The precipitate was filtered, washed the petroleum ether (50 ml) and dried in vacuo over P2 O5 at 40 for 16 hours to give 9.23 g of crude desired product which was then used in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1194-78-1, its application will become more common.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5126345; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia