Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 4983-28-2, 2-Chloro-5-hydroxypyrimidine, 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 2-Chloro-5-hydroxypyrimidine, blongs to pyrimidines compound. Safety of 2-Chloro-5-hydroxypyrimidine

600 mg (2.11 mmol) of example VII.1, 275 mg (2.11 mmol) 2-chloro-5-hydroxypyrimidine and 1.12 mL (6.53 mmol) DIPEA in 8 mL NMP are stirred at 150° C. for 6 h in a microwave oven. Afterwards the reaction mixture is directly purified by HPLC (MeOH/H2O/NH3).C18H22N4O3 (M=342.4 g/mol)ESI-MS: 343 [M+H]+Rt (HPLC): 1.04 min (method J)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4983-28-2, 2-Chloro-5-hydroxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEIMANN, Annekatrin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/315882; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 99979-77-8 ,Some common heterocyclic compound, 99979-77-8, molecular formula is C5H6ClN3O, 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 1Preparation of Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]-carbonothioylcarbamate (2) 2-Chloro-5-methoxypyrimidin-4-amine (1) (6.4 g, 0.040 mol) was suspended in ethyl acetate (100 mL) and heated to near reflux. Ethyl isothiocyanatidocarbonate (8.9 g, 1.7 eq) was added all at once, and the mixture was maintained at reflux for 10 hours. The resulting slurry was cooled to 15° C., and the solid product was isolated by filtration and the cake washed with fresh ethyl acetate to afford the title compound in several crops as a solid (7.8 g, 67percent): mp 182° C.; 1H NMR (DMSO-d6): delta 11.97 (s, 1H), 11.72 (s, 1H), 8.50 (s, 1H), 4.22 (q, 2H), 3.72 (s, 3H), 1.17 (t, 3H); 13C NMR (DMSO-d6): delta 177.82, 153.58, 150.00, 149.01, 144.26, 142.63, 62.76, 57.56, 14.44; Mass spec (accurate mass): Calcd for C9H11ClN4O3S: 290.024039; found, 290.0241.

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. 99979-77-8, 2-Chloro-5-methoxypyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW AGROSCIENCES LLC; US2011/295003; (2011); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 33097-11-9, 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.33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, molecular formula is C6H4Cl2N2OS, molecular weight is 223.0798, as common compound, the synthetic route is as follows.

To a solution of pyrimidine (1.55 g, 7.0 mmol) from step (a) in THF (20 mL) was added Et3N (1.5 equiv, 10.5 mmol, 1.5 mL). The solution was then cooled to 00C, followed by dropwise addition of ethyl-2-mercapto -acetate (1 equiv, 0.77 mL). The mixture was stirred for Ih at 00C. After this time, the reaction was concentrated, triturated with hexanes and filtered. The mother liquor was concentrated and subjected to silica gel chromatography (88:12 hexanes/ethyl acetate). Concentration of the desired fractions afforded 1.6g of the desired compound as a white solid (5.2 mmol, 75%). 1H NMR (CDCl3, 300 MHz) delta 10.43 (s, IH), 4.22 (q, 2H, J=7.2 Hz), 3.90 (s, 2H), 2.60 (s, 3H), 1.28 (t, 3H, J=7.2 Hz). CHN CaIcM fOr CiOHi1ClN2O3S2: C, 39.15; H, 3.61; N, 9.13. Found: C, 39.29; H, 3.50; N, 9.05.

Statistics shows that 33097-11-9 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
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.938443-20-0, name is 2,4,7-Trichloropyrido[2,3-d]pyrimidine, molecular formula is C7H2Cl3N3, molecular weight is 234.4699, as common compound, the synthetic route is as follows.Recommanded Product: 2,4,7-Trichloropyrido[2,3-d]pyrimidine

e) 4-Amino-2, 7-dichloropyridopyrimidines (Inter. 6); To a cooled (0-50C) stirred solution (0.1 M) of the trichloro substrate (Inter. 5)(1 equiv.) in CH2Cl2 was added diisopropylethylamine (1 equiv.) in a dropwise fashion. The appropriate amine (1 equiv.) was then added to the reaction mixture portionwise over the period of 1 hour. The solution was maintained at room temperature with stirring for a further 1 hour before the mixture was washed with water (2 x 1 reaction volume). The aqueous extracts were combined and extracted with CH2Cl2 (2 x 1 reaction volume). The organic extracts were then combined, dried (sodium sulphate), filtered and concentrated in vacuo to give an oily residue which solidified upon prolonged drying. The solid was triturated with diethylether and then filtered and the cake washed with cold diethyl ether to leave the title compound in suitable clean form to be used without any further purification.; Inter. 6a: 2,7-Dichloro-4-morpholin-4-yl-pyrido[2,3-d]pyrimidine; R4= morpholino; (92% yield, 90% purity) m/z (LC-MS, ESP): 285 [M+H]+ R/T = 3.90 mins

At the same time, in my other blogs, there are other synthetic methods of this type of compound,938443-20-0, 2,4,7-Trichloropyrido[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2007/60404; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26452-81-3, Adding some certain compound to certain chemical reactions, such as: 26452-81-3, name is 4-Chloro-6-methoxypyrimidine,molecular formula is C5H5ClN2O, 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 26452-81-3.

To a mixture of 1.5 g of 4-chloro-6-methoxypyrimidine, 1.2 mL of 2,2,3,3,3-pentafluoro-1-propanol and 10 mL of DMF,Under ice-cooling, 0.5 g of sodium hydride (oil, 60%) was added.The resulting mixture was stirred at 80 C. for 5 hours. Water was added to the resulting reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine,Dry over anhydrous sodium sulfate and concentrate under reduced pressure.The obtained residue was subjected to silica gel chromatography to obtain 1.78 g of Intermediate 2-8 shown below.

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. 26452-81-3, 4-Chloro-6-methoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; MURAKAMI, SHINICHIRO; (291 pag.)JP2018/76354; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-66-9, 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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. A new synthetic method of this compound is introduced below.

General procedure: Aryl Halide, tetrakis (triphenylphosphine)palladium or Palladium(II) bis(triphenylphosphine) dichloride (0.05 eq) and boronic acid orpinnacol ester (1.2 eq) were weighed out into a microwave vessel or sealed tube. Acetonitrile (3 mL/mmol) and a 1M aqueous solutionof Sodium Carbonate (3 eq) were added. The vessel was capped and heatedthermally3-18 hrs at 100 C. Upon completion, the reaction was cooled and crudeproduct was either triterated via addition of water and collection byfiltration or extracted with sat ammonium chloride and DCM. If the crudeproduct was an intermediate, it was taken into the next step in most cases w/ofurther purification or alternatively submitted for reverse phase HPLCpurification when it was a final product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-66-9, 2-Chloropyrimidine-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 38275-57-9, 5-Bromopyrimidine-2-carbonitrile, 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, 38275-57-9, blongs to pyrimidines compound. Quality Control of 5-Bromopyrimidine-2-carbonitrile

At 0 C, methylmagnesium bromide (1.4 M solution in toluene/THF (75:25, 21.35 mL, 29.9 mmol) was added to a THF (54.3 mL) solution containing 5-bromo-2-cyanopyrimidine (5 g, 27.2 mmol). The resulting mixture was stirred for 2 h at 0 C. Next, a saturated aqueous ammonium chloride solution was added followed by 3.0 N HCl to adjust the pH to 1. This solution was allowed to stir overnight. The pH was then adjusted to 7-8 with a saturated aqueous solution of K2CO3and the material was extracted with EtOAc and concentrated in vacuo. The product thus obtained was purified on silica gel eluting with a hexanes/EtOAc gradient (0-100%). Desired fractions were then pooled and concentrated in vacuo to provide the title compound. LCMS-ESI (pos.) m/z: 200.9 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,38275-57-9, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1005-37-4, 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 1005-37-4 as follows.

Stage 2 2-Amino-4-methylamino-6-chloropyrimidine 3-oxide STR29 4 g of 2-amino-4-methylamino-6-chloropyrimidine are suspended in 50 ml of ethanol. After having cooled to 10 C., 11.9 g of meta-chloroperbenzoic acid are added dropwise as a solution in 100 ml of ethanol. At the end of addition, room temperature is regained and stirring is continued for 3 hours. The reaction mixture is cooled to 5 C. and then filtered on sintered glass. The precipitate obtained is recrystallized from 160 ml of a 2/3-1/3 ethanol-water mixture. 1.60 g of 2-amino-4-methylamino-6-chloropyrimidine 3-oxide are obtained. Yield=36%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1005-37-4, its application will become more common.

Reference:
Patent; L’Oreal; US5772990; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 956034-07-4, 2,4-Dichlorofuro[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, Safety of 2,4-Dichlorofuro[3,2-d]pyrimidine, blongs to pyrimidines compound. Safety of 2,4-Dichlorofuro[3,2-d]pyrimidine

Step C: 2-Chloro-/V-(2,2,2-trifluoroethyl)furo[3,2-i/|pyrimidiTo a flask was added 2,4-dichlorofuro[3,2-i/]pyrimidine (0.80 g, 4.23 mmol, ArkPharm) and DMF (3.0 mL). 2,2,2-Trifluoroethanamine (1.05 g, 10.58 mmol, Acros) was added. The mixture was heated in a microwave at about 120 C for about 15 min. The mixture was diluted with Et20 (100 mL). The mixture was washed with water (3 x 25 mL). The combined aqueous layer was extracted with Et20 (2 x 50 mL). The combined organic layers were dried over Na2S04, filtered, and concentrated in vacuo. The residue was transferred neat and was purified by preparative TLC eluting with 3 :1 hexanes/EtOAc to give 2-chloro-A^-(2,2,2-trifluoroethyl)furo[3,2-i/]pyrimidin-4- amine (0.76 g, 71%): LC/MS (Table 2, Method h) Rt = 1.85 min; MS mix: 252, 254 (M+H)+.

The synthetic route of 956034-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; CALDERWOOD, David, J.; WILSON, Noel, S.; COX, Philip; HOEMANN, Michael, Z.; CLAPHAM, Bruce; MULLEN, Kelly, D.; VASUDEVAN, Anil; VILLAMIL, Clara I; LI, Bin; SOMAL, Gagandeep; WO2012/48222; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia