Tag: M.W:200-300

Reference of 959236-97-6 , The common heterocyclic compound, 959236-97-6, name is 4-Bromo-2-(methylthio)pyrimidine, molecular formula is C5H5BrN2S, 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 stirred 30% H202 (6g, 29.4 mmol, 1 eq) was added ammonium molybdate tetrahydrate (1.09g, 0.88mmol, 0.03eq) at 0C portion wise then stirred for 20min., and then a solution of 4-bromo-2-(methylthio)pyrimidine (6g, 29.41mmol, leq) slowly added at 0C then allowed to RT for 3h. Monitored by TLC, the reaction mixture was concentrated to crude residue, which was diluted with cold water then extracted with DCM (3X100mL). The combined organic layer was washed with 5% H2SC>4 solution and water then dried over Na2SC>4 and concentrated to crude compound. The crude compound was purified by column chromatography (silica gel, 100-200 mesh) using 0-40% EtOAc in pet ether as eluent to afford 4-bromo-2- (methylsulfonyl)pyrimidine (6g, 86%) as off-white solid. LCMS: [M+H]+ 238.84.

The synthetic route of 959236-97-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 53557-69-0, 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 53557-69-0, name is 6-Iodopyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

6-iodopyrimidin-4-amine (prepared as described in WO 2016071214, 5.83 g, 26.4 mmol) and (1,1,2,2,2Pentafluoroethy)(1,1OphenanthroNneKN1,KN1O)copper (15.1 g, 39.6 mmol) was suspended in dimethylformamide (95.0 mL) in a dried vial under argon. The resulting mixture was heated to 90C over night. The reaction mixture was cooled down to room temperature and filtered over Celite. The filter cake was rinsed with ethyl acetate and the resulting green suspension was washed with aqueous saturated sodium bicarbonate and ammonium hydroxide solution, and then brine. Drying over sodiumsulfate, filtration and concentration in vacuo gave the crude product which was purified by chromatography over silica gel to afford 6-(1,1,2,2,2-pentafluoroethyl)pyrimidin-4-amine. LC-MS: 214 (M+H), Rt: 0.67 min, 1H NMR (400 MHz, Chloroform) delta ppm 5.41 (br s, 2 H) 6.82 (d, J=1 .10 Hz, 1 1-1) 8.71 (s, 1 H)

According to the analysis of related databases, 53557-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; RENDLER, Sebastian; MUEHLEBACH, Michel; EMERY, Daniel; (109 pag.)WO2018/206348; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 395082-55-0, 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.395082-55-0, name is 2-Chloro-4-iodopyrimidine, molecular formula is C4H2ClIN2, molecular weight is 240.43, as common compound, the synthetic route is as follows.

A solution of 3-aminoindazole (670.5 mg, 5.0 mmol) and 2-chloro-3-iodopyrimidine (1.202 g, 5 mmol)((Chem Eur J 15, 1468 (2009)), in dry dioxan (25 mL), containing CuI (47.5 mg, 0.25 mmol) trans-1,2-diaminocyclohexane (114 mg, 1.0 mmol) and K3PO4 (1.06 g, 5 mmol) is refluxed under N2 for 24 hrs. (Bioorg Med Chem Letters 22, 4358 (2012)) The mixture is cooled to 25 C and quenched with water (50 mL) and extracted with ethyl acetate (3 x 25 mL), washed with water (2 x 25 mL) and saturated brine (25 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (Pet/EtOAc 10/1) to afford 3-amino-1-(2-chloropyrimidin-4-yl)-1H-indazole as a white solid.

Statistics shows that 395082-55-0 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-iodopyrimidine.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 70227-50-8, name is 2-(tert-Butyl)-4-chloro-5-nitropyrimidine, molecular formula is C8H10ClN3O2, 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. Quality Control of 2-(tert-Butyl)-4-chloro-5-nitropyrimidine

Compound 3.4 was dissolved in MeOH (1 mL) and ammonium hydroxide solution (1.5 mL) was added. The reaction mixture was stirred overnight. After removal of excess ammonia and MeOH, the mixture was extracted with chloroform. After drying with anhydrous sodium sulfate and removal of the solvent, compound 3.5 (89 mg, ~78%) was obtained and used without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 70227-50-8.

Reference:
Patent; SUNESIS PHARMACEUTICALS, INC.; WO2006/65703; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 31462-58-5, 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 31462-58-5, name is 5-Iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 10; Example 10.1; General Route; N-(1-(4-((4-(Pyrimidin-5-yloxy)phenyl)ethynyl)phenyl)propan-2-yl)acetamide; 28.1 mg (0.14 mmol) 5-iodopyrimidine, 40.0 mg (0.14 mmol) N-(1-(4-((4-hydroxy-phenyl)ethynyl)phenyl)propan-2-yl)acetamide (I76.1), 1.30 mg (0.07 mmol) CuI, 1.9 mg (0.14 mmol) N,N-dimethylglycine hydrochloride and 58.7 mg (0.18 mmol) Cs2CO3 are added to 1 mL dioxane. The reaction mixture is stirred at 90 C. for 2 h then filtered through a plug of silica gel and washed with DMF. The filtrate is purified by HPLC (MeOH/H2O/TFA).C23H21N3O2 (M=371.4 g/mol)ESI-MS: 372 [M+H]+ Rt (HPLC): 2.22 min (method M)

According to the analysis of related databases, 31462-58-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214785; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 220041-42-9, 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. 220041-42-9, name is tert-Butyl 2-chloropyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

In a 20 mE vial under nitrogen, tert-butyl 2-chloropyrimi- dine-4-carboxylate (0.200 g, 0.932 mmol), 4-methylpiperi- din-3-ol hydrochloride (0.185 g, 1.220 mmol) and triethylamine (0.52 mE, 3.73 mmol) were added to THF (14 mE) and the resulting mixture was stirred at 80 C. for 16 h. The cooled mixture was concentrated in vacuo and the residuewas purified on the ISCO using a 25 g Innoflash column (Hexane/EtOAc) to give tert-butyl 2-(3-hydroxy-4-methyl-piperidin-1-yl)pyrimidine-4-carboxylate (0.269 g, 98%) as ayellow oil which was a mixture of diastereomers. EC (Analytical MethodA): 2.081 mi ECMS (APCI): calcd forC,5H24N303 [M+H] mlz 294.18; found 294.2. ?H NMR (400 MHz, CDC13) 0 8.45 (d, J=4.7 Hz, 1H), 7.02 (d, J=4.7Hz, 1H), 4.87 (ddd, J=1.6, 4.5, 12.7 Hz, 1H), 4.74-4.63 (m, 1H), 3.30 (tt, J=4.8, 9.4 Hz, 1H), 2.98 (ddd, J=2.7, 12.1, 13.3Hz, 1H), 2.84 (dd, J=10.0, 12.7 Hz, 1H), 1.87-1.74 (m, 1H),1.70 (d, J=4.7 Hz, 1H), 1.66-1.57 (m, 1H), 1.61 (s, 9H),1.36-1.20 (m, 1H), 1.10 (d, J=6.7 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,220041-42-9, its application will become more common.

Reference:
Patent; UNIVERSITE DE MONTREAL; Martel, Alain; Tremblay, Francois; (65 pag.)US9598419; (2017); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 114040-06-1, 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. 114040-06-1, name is 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 3-bromo-5,7-dichloropyrazolo[l,5-a]pyrimidine (14.6 g, 55.3 mmol) in DCM (200 mL) was added cis-hydroxy-3- methylcyclobutane-l-methylamine (7.0 g, 60.9 mmol), and DIPEA (19.2 mL, 110.6 mmol). The reaction was stirred at rt for 16 h. Water and DCM were added to separate the phases and the aqueous phase was extracted with DCM. The combined organic extracts were dried over Na2S04, filtered and concentrated to give the title compound as a yellow solid (18.1 g, 95%). H NMR (400 MHz, CDCk) delta ppm 7.96 (s, 1 H), 6.60-6.49 (m, 1H), 5.99 (s, 1H), 3.47 (t, J = 6.0 Hz, 2H), 2.38-2.27 (m, 3H), 1.96-1.85 (m, 2H), 1.43 (s, 3H); MS ESI [M + H]+ 345.1, calcd for [Ci2Hi4BrClN40 + H]+ 345.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,114040-06-1, 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LAUFER, Radoslaw; NG, Grace; LI, Sze-Wan; PAULS, Heinz W.; LIU, Yong; PATEL, Narendra Kumar B.; WO2015/70349; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1060815-90-8, 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. 1060815-90-8, name is 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

A.21 (400 mg, 1.43 mmol), benzenesulphonyl chloride (272 muL, 2.13 mmol), DMAP (18 mg, 0.15 mmol) and Hnig base (350 muL, 2.17 mmol) are taken up in 10 mL DCM and stirred for 16 h at 200C. The solvent is eliminated in vacuo, the residue is purified by column chromatography (method prep. HPLC2; 10 % acetonitrile to 95 % in 12 min) and A.21-PG (HPLC-MS: tRet. = 1.98 min; MS(M+H)+ = 420; method FEC3) is obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1060815-90-8, 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; BOEHMELT, Guido; KOFINK, Christiane; KUHN, Daniel; MCCONNELL, Darryl; STADTMUELLER, Heinz; WO2010/7116; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 60331-15-9, Adding some certain compound to certain chemical reactions, such as: 60331-15-9, name is 4-Chloro-6-methoxy-2-methyl-5-nitropyrimidine,molecular formula is C6H6ClN3O3, 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 60331-15-9.

EXAMPLE 4 3-(6-Methoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine A solution of 0.204 g (1.0 mmol) of 2-methyl-4-methoxy-5-nitro-6-chloro-pyrimidine [Helv. (1958), 41, 1806], 0.20 g (1.1 mmol) 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride [J. Heterocycl. Chem. (1971), 8(5), 779-83] and 0.30 g (3.0 mmol) triethylamine in 10.0 ml N,N-dimethylformamide was stirred at room temperature for 60 h. The reaction mixture was then poured into 50 ml of an ice/water mixture and extracted three times with 60 ml of dichloromethane. The combined organic phases were washed twice with 50 ml of water, dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The residue obtained was then crystallized from dichloromethane/hexane to yield 0.28 g (0.9 mmol), 90%,3-(6-methoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow solid; m.p. 123-128 C.

According to the analysis of related databases, 60331-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6218385; (2001); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 943006-46-0, 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 943006-46-0, name is 4-Amino-6-iodo-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Part C: A mixture of 4-amino-6-diodo-2-methylpyrimidine (500 mg, 2.13 mmol) and NaH (60% dispersion in mineral oil, 170 mg, 4.25 mmol) in DMF (15 mL) was stirred at RT for 30 min. A solution of Intl-A (741 mg, 2.13 mol) in DMF (7 mL) was added, and the reaction mixture was stirred at RT for 1 h. The reaction mixture was poured into EtOAc (ca. 100 mL) and water (ca. 25 mL), IM aqueous HCl was added to give pH = 7, and the layers were separated. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography, elution with 40-75% EtOAc in hexanes, to give Int-6 (710 mg, 66%) as an off-white solid. LCMS (m/z): 503 (M+H)+

According to the analysis of related databases, 943006-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ICAGEN, INC.; WO2007/75852; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia