Month: August 2021

Reference of 3435-25-4 ,Some common heterocyclic compound, 3435-25-4, molecular formula is C5H5ClN2, 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.

A solution of BA-1 (1.00 g, 7.78 mmol), and Ni(dppe)Cl2 (82 mg, 0.16 mmol) in anhydrous Et20 (5 mL) is cooled to -10 C. A solution of isopropyl magnesium bromide (3.22 mL, 9.33 mmol) is added dropwise and the mixture is stirred for 1 h at -10 C. The mixture is quenched with sat. NH4C1, extracted with DCM and concentrated. The crude BC-1 is carried on as is.

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. 3435-25-4, 4-Chloro-6-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BAKONYI, Johanna; BRUNETTE, Steven Richard; COLLIN, Delphine; HUGHES, Robert Owen; LI, Xiang; LIANG, Shuang; SIBLEY, Robert; TURNER, Michael Robert; WU, Lifen; ZHANG, Qiang; WO2015/160654; (2015); 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.14001-66-2, name is 5-Bromo-2-methoxypyrimidine, molecular formula is C5H5BrN2O, molecular weight is 189.01, as common compound, the synthetic route is as follows.SDS of cas: 14001-66-2

General procedure: To a well stirred solution of substituted internal alkenyltrifluoroborate and the aryl/heteroarylbromides, Cs2CO3 in toluene/H2O (10:1) was added Pd(PPh3)4 and heated to reflux. After 16 h, the reaction was cooled to room temperature and diluted with water. The reaction mixture was extracted with ethyl ether (3x mL). The organic layer was washed with 2N HCl. The aqueous layer was washed with ether and then neutralized with 2N NaOH and extracted with ethyl ether. The organic layer was dried (Na2SO4). The solvent was removed in vacuo and this usually gave clean product. If necessary the crude material was further purified by silica gel column chromatography (elution with EtOAc/MeOH 19:1): The products were usually obtained as a clear pale yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14001-66-2, 5-Bromo-2-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Math, Shivanand K.; Mokri, Homayoun H.; Lamunyon, James B.; Cefalo, Dustin R.; Testa, Charles A.; Tetrahedron Letters; vol. 53; 23; (2012); p. 2847 – 2849;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 58347-49-2, 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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

A solution of 7-chloropyrazolo[i,5-ajpyrimidine (0.1 g, 0.651 mmol), 6- bromo-3-fluoro-2-methylpyridine (0.124 g, 0.651 mmol) and 1,1,1,2,2,2- hexamethyldistannane (0.213 g, 0.651 mmol) in 1,4-dioxane (2 mL) was purged withnitrogen gas for 10 mm. Pd(Ph3P)4 (0.075 g, 0.065 mmol) was added to the reaction mixture and the solution was purged with nitrogen gas again for 10 mm. The reaction mixture was heated in a microwave at 150C for 2 h. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate (20 mL) and water (20 mL). The biphasic mixture was filtered through diatomaceous earth (Diatomaceous earth) and the bed was washed with ethyl acetate (25 mL). The ethyl acetate layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a brown colored solid. The solid was purified by silica gelchromatography (0-40% EtOAc in pet ether) to afford 7-(5-fluoro-6-methylpyridin-3- yl)pyrazolo[1,5-ajpyrimidine (0.06 g, 0.263 mmol, 40% yield) as a light yellow solid. LCMS (ESI) m/e 228.22 [(M+H), calcd for C12H9FN4 229.2j; LC/MS retention time (Method Al): tR = 2.20 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 33034-67-2, 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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, 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 tert-butyl 4-({ [4-(5-cyano-7-isopropyl- 1 ,3-benzoxazol-2- yl)benzoyl] amino }methyl)-4-isopropylpiperidine- 1 -carboxylate(35 mg, 0.064 mmol) in dichloromethane was added trifluoroacetic acid. The mixture was stirred overnight at room temperature and then concentrated in vacuo. To the residue were added of methanol (2 ml), potassium carbonate (45 mg, 0.326 mmol) and 2-chloro-4- (trifluoromethyl)pyrimidine (16 mul, 0.133 mmol). The mixture was heated to 50 0C and stirred at this temperature for 4 h, at which point LC/MS analysis showed a peak at the desired molecular weight. The reaction mixture was concentrated and then purified by flash chromatography on a Biotage Horizon, 25S column, eluting with 1 column volume of 100percent dichloromethane followed by a gradient of 0 to 100percent ethyl acetate in dichloromethane over 10 column volumes to provide the title compound (33 mg, 0.056 mmol, 87 percent yield). Mass spectrum (ESI) 591.1 (M+l). 1HNMR (500 MHz, CDCI3): 8.47 (d, J=4.5 Hz, IH), 8.33 (d, J=8.5 Hz, IH), 7.93 (s, IH), 7.92 (d, J= 8.5 Hz, 2H), 7.51 (s, IH), 6.71 (d, J=5.0 Hz, IH), 6.18 (br t, J = 6.0 Hz, IH), 4.18 (m, 2H), 3.65-3.75 (m, 4H), 3.47 (septet, J = 7.0 Hz, IH), 1.89 (septet, J=6.5 Hz, IH), 1.70 (m, 2H), 1.50- 1.60 (m, 2H), 1.46 (d, J = 6.5 Hz, 6H), 1.02 (d, J=7.0 Hz, 6H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 33034-67-2, 2-Chloro-4-(trifluoromethyl)pyrimidine.

Reference:
Patent; MERCK & CO., INC.; WO2008/156715; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 6237-96-3, 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. 6237-96-3, name is 4,6-Dichloro-2-ethylpyrimidin-5-amine, molecular formula is C6H7Cl2N3, 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.

EXAMPLE 128 6-Chloro-5,6-diamino-2-ethylpyrimidine The material prepared in the foregoing Example 127 (6.19 g, 32 mmol) was dissolved in 2-propanol (75 ml) and 10 ml of anhydrous ammonia was added. This was sealed in a pressure vessel and heated at 110 for 4 hr. The mixture was vented and then evaporated to a solid residue under a stream of nitrogen. This residue was leached with CH2 Cl2 (3*10 ml) and the soluble material (3 g) was shown (tlc, EtOAc:hexanes, 1:1) to be predominantly unreacted starting material, whereas the insoluble material (3.29 g, 19 mmol) was chromatographically pure title compound, suitable for the next reaction (Yield, 60%; quantitative, based on recovered starting material).

According to the analysis of related databases, 6237-96-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US5057517; (1991); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 956034-07-4, name is 2,4-Dichlorofuro[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below., category: pyrimidines

2,4-Dichlorofuro[3,2-d]pyrimidine 37 (23 mg, 1.0 eq) was suspended in methanol (1.7 ml) and treated with morpholine (0.09 ml, 4.0 eq). Reaction mixture was stirred at room temperature for 2 h, before being quenched with saturated aq. NaHCO3. Mixture was extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated to yield 2-chloro-4-morpholinofuro[3,2-d]pyrimidine 38 (14 mg, 48%) which was used in the next reaction without further purification.

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, 956034-07-4, 2,4-Dichlorofuro[3,2-d]pyrimidine.

Reference:
Patent; PIRAMED LIMITED; GENENTECH, INC.; BAYLISS, Tracy; CHUCKOWREE, Irina; FOLKES, Adrian; OXENFORD, Sally; WAN, Nan, Chi; CASTANEDO, Georgette; GOLDSMITH, Richard; GUNZNER, Janet; HEFFRON, Tim; MATHIEU, Simon; OLIVERO, Alan; STABEN, Steven; SUTHERLIN, Daniel, P.; ZHU, Bing-Yan; WO2008/70740; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 23956-12-9 ,Some common heterocyclic compound, 23956-12-9, molecular formula is C6H8N2O3, 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.

General procedure: To a solution of dry 2 (140 mg, 0.897 mmol) and K2CO3 (619.6 mg, 4.48 mmol) in anhydrous DMF (10 mL) at 15 C MOMCl (0.27 mL, 3.56 mmol) was added. Reaction mixture was stirred at r.t. overnight. Solvent was evaporated in vacuo and residue was purified by column chromatography (CH2Cl2 : MeOH = 20 : 1) to yield white powder of 12a (42.7 mg, 23.8 %, m.p. = 124126 C), colorless oil of 12b (26.5 mg, 14.8 %) and white powder of 12c (5.4 mg, 2.5 %, m.p. = 9294 C). 12a: 1H-NMR: 11.01 (1H, s, NH-3), 7.29 (1H, s, H-6), 5.17 (2H, s, CH2-N1), 4.55 (1H, t, J = 5.30 Hz, OH), 3.47 (2H, q, J = 6.14 Hz, H-2′), 3.27 (3H, s, OCH3-N1), 2.36 (2H, t, J = 6.54 Hz, H-1′). 13C-NMR: 164.43 (C-4), 151.49 (C-2), 142.04 (C-6), 111.00 (C-5), 77.93 (CH2-N1), 59.73 (C-2′), 56.45 (OCH3-N1), 30.27 (C-1′). ESI-MS 201 [M+H]+. Anal. calcd. For C8H12N2O4: C 48.00, H 6.04. Found: C 47.94, H 6.06. 12b: 1H-NMR: 10.81 (1H, s, NH-1), 7.54 (1H, s, H-6), 5.26 (2H, s, CH2-N3), 4.48 (1H, t, J = 5.62 Hz, OH), 3.53 (2H, t, J = 6.20 Hz, H-2′), 3.22 (3H, s, OCH3-N3), 2.38 (2H, t, J = 6.55 Hz, H-1′). 13C-NMR: 164.92 (C-4), 151.78 (C-2), 139.46 (C-6), 109.11 (C-5), 65.93 (CH2-N3), 59.69 (C-2′), 55.04 (OCH3-N3), 26.99 (C-1′). ESI-MS 201 [M+H]+. Anal. calcd. For C8H12N2O4: C, 48.00; H, 6.04. Found: C 48.07, H 6.06. 12c: 1H-NMR: 7.63 (1H, s, H-6), 5.21 (2H, s, CH2-N1), 5.08 (2H, s, CH2-N3), 4.60 (1H, t, J = 5.49 Hz, OH), 3.29 (3H, s, OCH3-N1), 3.28 (3H, s, OCH3-N3), 3.51 (2H, q, J = 6.16 Hz, H-2′), 2.40 (2H, t, J = 6.51 Hz, H-1′). 13C-NMR: 164.23 (C-4), 151.72 (C-2), 141.55 (C-6), 110.21 (C-5), 79.11 (CH2-N1), 71.99 (CH2-N3), 59.56 (C-2′), 57.38 (OCH3-N1), 56.64 (OCH3-N3), 30.79 (C-1′). ESI-MS 245 [M+H]+. Anal. calcd. For C10H16N2O5: C 49.17, H 6.60. Found: C 49.09, H 6.59.

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. 23956-12-9, 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kraljevi?, Tatjana Gazivoda; Klika, Mateja; Kralj, Marijeta; Martin-Kleiner, Irena; Jurmanovi?, Stella; Mili?, Astrid; Padovan, Jasna; Rai?-Mali?, Silvana; Bioorganic and Medicinal Chemistry Letters; vol. 22; 1; (2012); p. 308 – 312;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4316-98-7, name is 6-Chloro-4,5-diaminopyrimidine, the common compound, a new synthetic route is introduced below. COA of Formula: C4H5ClN4

Step 2: 6-Chloro-8-propylpurine To a solution of 4,5-diamino-6-chloropyrimidine (0.289 g, 2 mmol) in 2-methoxyethanol (10 ml) were added trimethylorthobutyrate (0.5 ml, 3 mmol) and p-toluenesulfonic acid (0.03 g), and the mixture was refluxed for 18 hours and then concentrated in vacuo. The residue was partitioned between water and ethylacetate. The organic phase was then washed with brine and dried (MgSO4). The crude product obtained after evaporation of the solvent was purified by flash column chromatography on silica-gel using ethylacetate/hexane (1:1).

The synthetic route of 4316-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5102880; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 109229-22-3, 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. 109229-22-3, name is 6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

Preparation 26-Benz l-4-bromo-5,6,7,8-tetrahydropyrido[4,3-rf]pyriniidinePOBr3 (8.92 g, 21 x 1.5mmol) was added to a slurry of the title compound from Preparation 1 (5 g, 21 mmol) in dichloroethane (100 mL). The mixture was stirred at room temperature for 1 h and then refluxed and stirred for a further 1 h, during which time the course of the reaction was monitored by TLC (Merck UV-254; chloroform/methanol 10:1; samples were treated with saturated Na2C(? solution). The reaction mixture was cooled to room temperature, treated with saturated Na2CC>3 solution, stirred for 10 min and treated with ultrasound for 10 min. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layers were combined, washed with water, dried over MgS04 and evaporated to give the product in 79% (5 g) yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109229-22-3, 6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER, INC.; LONG, Scott, A.; THORARENSEN, Atli; SCHNUTE, Mark, E.; WO2013/54185; (2013); 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.155-10-2, name is 4-Amino-2-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, molecular weight is 147.5381, as common compound, the synthetic route is as follows.SDS of cas: 155-10-2

Step 3. l-(4-Amino-5-fluoro-pyrimidin-2-yl)-3-trifluoromethyl-lH-pyrazole-4-carboxylic acid (adamantan- 1 -ylmethy l)-amide; A solution of 3-trifluoromethyl-lH-pyrazole-4-carboxylic acid (adamantan- 1- ylmethyl)-amide (100 mg, 0.306 mmol), 2-chloro-5-fluoro-pyrimidin-4-ylamine (52 mg, 0.35 mmol) and Cs2CO3 (130 mg, 0.4 mmol) in NMP (1.0 mL) is heated in a microwave reactor at150 C for 1 h. The mixture is poured into H2O. The crude product is filtered out, dissolved in 10% MeOH in DCM, and dried over anhydrous Na2SO4. The title compound is purified byPTLC (eluted with 5% MeOH in DCM). 1H NMR (CD3OD): 8.96 (s, IH), 8.1 l(s, IH), 3.0 (s, 2H), 1.98 (m, 3H), 1.78-1.68 (m, 6H), 1.58 (s, 6H). MS (M+l) = 439.29; Rtau = 1.34 min.*IC50.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,155-10-2, 4-Amino-2-chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROGEN CORPORATION; WO2009/12482; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia