Pyrimidines

Synthetic Route of 1211443-61-6, 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 1211443-61-6 as follows.

A mixture of 2-chloro-7-cyclopentyl–N, N- dimethyl -7H- pyrrolo [2,3-d] pyrimidine-6-carboxamide (200mg, 0.68mmol), 5- (2- oxazolyl -7- aza-spiro [3.5]Nonane-1-yl) -2-amino-pyridine (0.17g, 0.78mmol), Cs2CO3 (0.20g, 1mmol), BINAP (20mg, 0.03mmol) andPd (OAc) 2 (10mg, 0.03mmol) was added mixed in 1,4-dioxane (30mL), purged with N2 at 95 react overnight.The reaction solutionAfter cooling, water was added (20 mL), and extracted with dichloromethane (40mL × 3), the organic phase was washed with water (15mL) washed with saturated brine (15mL) wash,Dried over anhydrous sodium sulfate, filtered, concentrated and the crude product is purified by silica gel column chromatography (methylene chloride / methanol (V / V) = 20/1), with methanolRecrystallized yellow solid (50mg, 15.4%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1211443-61-6, its application will become more common.

Reference:
Patent; East Sunshine Pharmaceutical Co., Ltd.; Liu, Bing; Zhang, Yingjun; Nie, Linlin; Bai, Shun; Zheng, Changchun; Nie, biao; Li, Zhiyong; Tan, Yumei; (61 pag.)CN105294737; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.76196-80-0, name is Methyl 5-methylpyrimidine-2-carboxylate, molecular formula is C7H8N2O2, molecular weight is 152.1506, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl 5-methylpyrimidine-2-carboxylate

To a solution of 211 methyl 5-methylpyrimidine-2-carboxylate [Example 9, Step 2] (2.5 g, 16.4 mmol, 1.00 equiv) in 89 methanol (40 mL) was added 212 NaBH4 (1.87 g, 49.3 mmol, 3.00 equiv) at 0 C. The resulting solution was stirred for 3 h at 25 C. The reaction was then quenched by the addition of 24 H2O (40 mL). The resulting mixture was concentrated under vacuum to remove MeOH. The resulting solution was extracted with ethyl acetate (3×50 mL). The organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 1.3 g (63.9%) of 189 (5-methylpyrimidin-2-yl)methanol as a yellow solid. LC-MS: m/z=125 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76196-80-0, Methyl 5-methylpyrimidine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; ZHANG, Chengzhi; (94 pag.)US2018/79742; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 54738-73-7 ,Some common heterocyclic compound, 54738-73-7, molecular formula is C5H3BrN4O, 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.

3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate A) (15.08 g, 70.5 mmol) was suspended in 189 ml of phosphous oxychloride. Diethylaniline (19 ml, 119.4 mmol) was added and the resulting reaction mixture was heated to 106 C. for 2 hours. After cooling to room temperature, the solvent was removed and the resulting amber syrup was poured to 300 ml of ice-water. 20 minutes later, the aqueous layer was extracted with diethyl ether (500 ml*4). The combined organic layer was washed, dried and evaporated to give 6.87 g of 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine as light yellow solid. 1H NMR (DMSO) 8.857 (s 1H), 14.84 (bs, 1H); LC/MS (MH+=233).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54738-73-7, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6921763; (2005); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 91717-22-5, Adding some certain compound to certain chemical reactions, such as: 91717-22-5, name is 2-Amino-4-piperidino-6-methylpyrimidine,molecular formula is C10H16N4, 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 91717-22-5.

In a 100 mL jar, 2-amino-4-piperidinyl-6-methylpyrimidine (0.001 mol) was added,P-tolualdehyde (0.001 mol) and dimethyl malonate (0.0015 mol) were added with p-xylene (30 mL) as a solvent. The reaction was terminated in microwave at 100C for 50 minutes, and paraxylene was recovered under reduced pressure.Column chromatography (petroleum ether:ethyl acetate=4:1 V/V) gave the desired product.

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. 91717-22-5, 2-Amino-4-piperidino-6-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guizhou Institute Of Technology; Bai Song; Zhu Yunying; Wei Xian; Wu Qin; Zou Shuliang; Tang Qin; Gong Zhihai; Zhou Han; Zhou Hang; (14 pag.)CN108101855; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, molecular weight is 154.5571, as common compound, the synthetic route is as follows.Computed Properties of C5H3ClN4

Example 2 Preparation of 4-(1H-pyrazolo-4-phenoxy)aniline (3a-1) P-aminophenol (0.55g, 5.5mmol) and sodium hydroxide (0.20g, 5.5mmol) were added to 10mL water; potassium carbonate (0.76g, 5.5mmol) was added after resulting mixture was stirred for 30 minutes at normal temperature; the temperature was increased to 60C, and tetrahydrofuran solution of 4-chloro-1H-pyrazolopyrimidine (intermediate 2) (0.94g, 6.6mmol) was slowly added to the reaction solution; after one hour, reaction was stopped; after the tetrahydrofuran of the reaction system was distilled to dryness, the remaining system was extracted with ethyl acetate and water twice; the ethyl acetate layer was dried with anhydrous magnesium sulfate and then spun dry, and then introduced into a column for purification to obtain 0.77g 4-(1H-pyrazolo-4-phenoxy)aniline (3a-1) at a yield of 62.1%. 1H NMR (400 MHz, DMSO-d6): delta 14.07(s, 1H), 8.50(s, 1H), 7.67(s, 1H), 6.96(d, J=8.8 Hz, 2H), 6.64(d, J=8.8 Hz, 2H), 5.20(s, 2H) ppm. LCMS m/z: 228.1 [M + H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GUANGXI WUZHOU PHARMACEUTICALS (GROUP) CO., LTD.; YANG, Shengyong; WEI, Yuquan; EP2889298; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5305-59-9, Adding some certain compound to certain chemical reactions, such as: 5305-59-9, name is 6-Chloropyrimidin-4-amine,molecular formula is C4H4ClN3, 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 5305-59-9.

A mixture of 4-(4-bromothiazolo[5,4-c]pyridin-2-yl)-3,5-dichlorobenzonitrile (0.250 g, 0.65 mmol), 4-amino-6-chloropyridine (0.080 g, 0.62 mmol), Pd2(dba)3 (0.030 g, 0.033 mmol), XantPhos (0.038 g, 0.065 mmol) and cesium carbonate (0.530 g, 1.60 mmol) in dioxane (6.5 mL) was degassed with nitrogen then heated at 70 C for 4 hours. The resulting mixture was diluted with DCM and water, and then filtered through Celite. The layers of the filtrate were separated and the organic layer, dried over Na2S04 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0- 25% EtOAc in pentane and 0-10% EtOAc in DCM to give the desired compound as a yellow solid (0.215 g, 76% yield). ¾ NMR (300 MHz, DMSO-t¾: delta 11.16 (s, 1H), 8.65 (s, 1H), 8.52 (d, J= 5.6 Hz, 1H), 8.39 (s, 2H), 7.97 (s, 1H), 7.91 (d, J= 5.6 Hz, 1H). LCMS (Method E): RT = 3.83 min, m/z: 433 [M+H+].

According to the analysis of related databases, 5305-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22177-99-7, 4-(6-Chloro-2-methylpyrimidin-4-yl)morpholine, 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, 22177-99-7, blongs to pyrimidines compound. Quality Control of 4-(6-Chloro-2-methylpyrimidin-4-yl)morpholine

2-Methyl-4-chloro-6-morpholino-pyrimidine (10.7 g.; 50 mmol) was dissolved in tetrahydrofuran (200 mL). The reaction was chilled to -78C under an inert atmosphere. A solution of n-butyllithium in hexanes (25 mL, 2.5M, 62.50 mmol) was added, and the reaction mixture was stirred for thirty minutes. A solution of isobutylene oxide 6.6 mL, 75 mmol) was added, and the reaction was allowed to warm to room temperature while stirring overnight. The solvent was removed under reduced pressure, and the crude material was dissolved in methylene chloride (200 mL) and washed with saturated ammonium chloride (2×50 mL), dried with sodium sulfate, and evaporated to dryness. The compound was purified by column chromatography to give 4-(4-chloro-6-morpholin- 4-yl-pyrimidin-2-yl)-2-methyl-butan-2-ol (6.2 g., 21.7 mmol).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22177-99-7, its application will become more common.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/124662; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 147118-37-4, 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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide. A new synthetic method of this compound is introduced below.

(1) Synthesis of 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-acrylonitrile Add 30 g of 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-formaldehyde into a reaction flask of 500 ml, add toluene 130 ml, and start to agitate. Add in turn phosphate diethylacetonitrile 20.5 g and Aliquat336 (catalyst) 1.4 g, and titrate with 20% sodium hydroxide solution 62.7 g below 25 C., with the reaction solution gradually clarifying and turning out to be a pink clear solution after titration. React for 3 hours at room temperature, and a white solid precipitates. Filter with a pump, wash with water, pump, and dry, and obtain a white solid 30.5 g with a yield of 95.4%. Add 30 g of 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-formaldehyde into a reaction flask of 500 ml, add toluene 140 ml, and start to agitate. Add in turn phosphate diethylacetonitrile 16.4 g and Aliquat336 1.6 g, and titrate with 20% sodium hydroxide solution 60.5 g below 25 C., with the reaction solution gradually clarifing and turning out to be a pink clear solution. React for 4 hours at room temperature, and a white solid precipitates. Filter with a pump, wash with water, drain with a pump, dry, and obtain a white solid 28.5 g, with a yield of 89.1%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147118-37-4, N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Anhui Quingyun Pharmaceutical and Chemical Co., Ltd.; US2008/91014; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.1005-38-5, name is 4-Amino-6-chloro-2-(methylthio)pyrimidine, molecular formula is C5H6ClN3S, molecular weight is 175.64, as common compound, the synthetic route is as follows.COA of Formula: C5H6ClN3S

Quinoline-4-carboxylic acid (36.4 mg, 0.226 mmol),3-chloro-5-(methylthio)benzene amine (50.0 mg, 0.205 mmol)and POCl3 (34.6 mg, 0.226 mmol)Dissolved in pyridine (1 mL)and stirred at 80C for 1 hour. Thin film chromatography (TLC) in verifying, new spot the system is moved, and adding water to the composition, a reaction mixture of a, die chloro methane at extracted times 2. The organic layer extracted are dried, using magnesium sulfate, after, concentrating it under reduced pressure, organic for extract of moisture MgSO4removal of filtering the concentrate and a thin silica gel fraction is concentrated to after chromatography (preparative TLC, n/ethyl acetate = 1/1-hexanediol) for purifying the white solid thereby, a desired compound (11%) is obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1005-38-5, 4-Amino-6-chloro-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Korea research Institute of Chemical Technology; Han, Soo Bong; Achari, Ragavendra; Kim, Mi Hyeon; Jong, Yong Sik; Kim, Pil Ho; (119 pag.)KR2016/21163; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 65996-58-9, Adding some certain compound to certain chemical reactions, such as: 65996-58-9, name is 2-Amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one,molecular formula is C6H6N4O, 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 65996-58-9.

General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.

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. 65996-58-9, 2-Amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Rodrigues, Marili V.N.; Barbosa, Alexandre F.; Da Silva, Julia F.; Dos Santos, Deborah A.; Vanzolini, Kenia L.; De Moraes, Marcela C.; Correa, Arlene G.; Cass, Quezia B.; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 226 – 231;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia