Day: June 11, 2021

Application of 1224288-95-2 ,Some common heterocyclic compound, 1224288-95-2, molecular formula is C7H4N4O, 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 mixture of 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (1.33 g, 8.31 mmol) and POCl3 (7.74 mL, 83 mmol) was heated at 150 C. for 3 hours and cooled to room temperature. After concentration in vacuo, the residue was purified by column chromatography on SiO2 (Hex:EtOAc=2:1) to afford 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonitrile (343 mg, 23%) as a white solid. 1H-NMR (CDCl3, Varian, 400 MHz): delta 7.09 (1H, d, J=7.6 Hz), 8.39 (1H, s), 8.68 (1H, d, J=7.2 Hz).

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. 1224288-95-2, 5-Oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HANDOK INC.; CMG Pharmaceutical Co., Ltd.; Kim, Moonsoo; Lee, Chaewoon; Lee, Gilnam; Yoon, Cheolhwan; Seo, Jeongbeob; Kim, Jay Hak; Lee, Minwoo; Jeong, Hankyul; Choi, Hyang; Jung, Myung Eun; Lee, Ki Nam; Kim, Hyun Jung; Kim, Hye Kyoung; Lee, Jae Il; Lee, MinWoo; Kim, Misoon; Choi, Soongyu; (124 pag.)US2016/168156; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)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, SDS of cas: 153435-63-3, blongs to pyrimidines compound. SDS of cas: 153435-63-3

(S)-(5-(((5-chloropyridin-2-yl)amino)methyl)-6-azaspiro[2.5]octan-6-yl)(5-fluoro-2-(pyrimidin-2-yl)phenyl)methanone Intermediates 4 (1 eq) was dissolved dry DMF (20 ml/mmol), then CsF (2 eq), CuI (0.2 eq), [Ph3P]4Pd (0.1 eq) and 2-(tributylstannyl)pyrimidine (1.5 eq; prepared according to Eur. J. Org. Chem. 2003, 1711-1721) was added. The mixture was warmed at 130 C. for 10 minutes (microwave), then poured in aqueous saturated solution of NH4Cl and extracted with AcOEt. The organic layers were combined, dried (Na2SO4) and concentrated under vacuum; crude product was purified by silica gel column chromatography (DCM to DCM/MeOH 9/1) to obtain the title compound with yield of 15%. 1HNMR (CDCl3) delta ppm 8.80-8.93 (m, 1H), 8.64 (d, 1H), 8.24-8.50 (m, 1H), 7.83-8.08 (m, 1H), 6.89-7.40 (m, 4H), 6.17-6.56 (m, 1H), 5.11-5.25 (m, 1H), 4.3-4.9 (m, 1H), 3.6-4.0 (m, 2H), 3.01-3.47 (m, 2H), 1.92-2.38 (m, 1H), 1.45-1.8 (m, 1H), 0.65-1.12 (m, 1H), 0.17-0.59 (m, 4H). ESI+m/z 474 [M+Na]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ROTTAPHARM S.P.A.; Stasi, Luigi Piero; Rovati, Lucio; US2013/310400; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 956034-07-4, 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.956034-07-4, name is 2,4-Dichlorofuro[3,2-d]pyrimidine, molecular formula is C6H2Cl2N2O, molecular weight is 188.9989, as common compound, the synthetic route is as follows.

Under nitrogen, to a suspension of compound 5-a (640 mg, 1.65 mmol), compound 30-c (280 mg, 1.49 mmol) and potassium carbonate (720 mg, 5.2 mmol) in 1,4-dioxane (2 mL) and water (6 mL) was added Pd(PPh3)4 (57 mg, 0.05 mmol), the mixture was heated to 80 C. and stirred for 16 hours. The mixture was then concentrated under reduced pressure, the residue was diluted with water (20 mL), extracted with dichloromethane (20 mL×3). The organic layer were combined, washed with water (10 mL×3) and saturated brine (10 mL) in sequence, then dried over anhydrous sodium sulfate, filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate=3:1) to give light yellow solid 30-b (620 mg, yield: 70%). LC-MS (ESI): nm/z=415 [M+H]+.

Statistics shows that 956034-07-4 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichlorofuro[3,2-d]pyrimidine.

Reference:
Patent; SHANGHAI CHEMEXPLORER CO., LTD.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WANG, Tinghan; US2015/336982; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 695-85-2, 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. 695-85-2, name is 4-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

1-(t-Butoxycarbonyl)-4-(5-methoxy-4-pyrimidyl)-3-methylpiperazine A mixture of 1-(t-butoxycarbonyl)-3-methylpiperazine (2.0 g, 0.01 mole), 4-chloro-5-methoxypyrimidine (1.5 g, 0.01 mole) and diisopropylethylamine (2.6 mL, 0.015 mole) in 25 mL of dry acetonitrile was heated to reflux under Ar for 60 h. The resulting solution was diluted with ether and then washed (H2 O, brine), dried (Na2 SO4) and evaporated to give a gum. This gum was triturated with hexane (x3) and the supernatant was evaporated to give a gum. Flash chromatography (SiO2 /ethyl acetate-hexane=1:1, then ethyl acetate) of this material gave first 4-chloro-5-methoxypyrimidine (0.4 g, 27%) and then the desired product (1.2 g, 30%) as a light pink solid: m.p. 70-72 C.; IR (KBr) 1690, 1575 cm-1; 1 H nmr (200 MHz, CDCl3) delta 8.33 (s, 1H), 7.90 (s, 1H), 4.79 (br s, 1H), 4.4-3.8 (m, 3H), 3.86 (s, 3H), 3.35-2.90 (m, 3H), 1.48 (s, 9H), 1.21 (d, J=6.7 Hz, 3H).

According to the analysis of related databases, 695-85-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US5434154; (1995); A;,
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. 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. Computed Properties of C5H4Cl2N2S

Prepared by methods substantially similar to those set forth in Koppell et al, JOC, 26,1961, 792, in the following manner. To a stirred solution of 4, 6-dichloro-2- (methylthio) pyrimidine (50 g, 0.26 mol) in dichloromethane [(1] L) at [0C] was added meta-chloroperoxybenzoic acid (143.6 g, 0.64 mol) over a period of 20 minutes. The solution was allowed to warm to room temperature and was stirred for 4 hours. The mixture was diluted with dichloromethane (1.5 L) and then treated sequentially with 50% [NA2S203/NAHC03] solution (2 x 200 ml), sat. [NAHC03] solution (4 x 300 ml), and brine (200 ml) then dried [(MGS04).] The solvent was removed in vacuo to afford an off-white solid which was redissolved in EtOAc [(1 L)] and treated sequentially with sat. [NAHC03] solution (3 x [300] ml), and brine (100 [ML)] then dried (MgS04). The solvent was removed in vacuo to afford the title compound (A) as a white solid (55.6 g, 96% yields NMR [CDC13] [5] 3.40 (3H, s, CH3), 7.75 [(1H.] s. ArH).

The synthetic route of 6299-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/833; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 695-85-2, 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.695-85-2, name is 4-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.

1-(t-Butoxycarbonyl)-4-(5-methoxy-4-pyrimidyl)-3-methylpiperazine A mixture of 1-(t-butoxycarbonyl)-3-methylpiperazine (2.0 g, 0.01 mole), 4-chloro-5-methoxypyrimidine (1.5 g, 0.01 mole) and diisopropylethylamine (2.6 mL, 0.015 mole) in 25 mL of dry acetonitrile was heated to reflux under Ar for 60 h. The resulting solution was diluted with ether and then washed (H2O, brine), dried (Na2SO4) and evaporated to give a gum. This gum was triturated with hexane ( 3) and the supernatant was evaporated to give a gum. Flash chromatography (SiO2/ethyl acetate-hexane=1:1, then ethyl acetate) of this material gave first 4-chloro-5-methoxypyrimidine (0.4 g, 27%) and then the desired product (1.2 g, 30%) as a light pink solid: m.p. 70-72 C.; IR (KBr) 1690, 1575 cm-1; 1H nmr (200 MHz, CDCl3) delta8.33 (s, 1H), 7.90 (s, 1H), 4.79 (br s, 1H), 4.4-3.8 (m, 3H), 3.86 (s, 3H), 3.35-2.90 (m, 3H), 1.48 (s, 9H), 1.21 (d, J=6.7 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 695-85-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Fabre-Kramer Pharmaceuticals, Inc.; US2009/281114; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3435-25-4, Adding some certain compound to certain chemical reactions, such as: 3435-25-4, name is 4-Chloro-6-methylpyrimidine,molecular formula is C5H5ClN2, 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 3435-25-4.

A solution of 6-methoxy-7-(2-(methylamino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (363 mg, 1 mmol) and 4-chloro-6-methylpyrimidine (257 mg, 2 mmol), (J. Het. Chem., 1969, 6, 879), in N,N-diisopropylethylamine (2 ml) was heated at reflux for 30 minutes. The volatiles were removed by evaporation and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluding with methylene chloride/methanol (95/5) to give 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (365 mg, 80%). 1 H NMR Spectrum: (CDCl3) 1.19(s, 9H); 2.36(s, 3H); 3.18(s, 3H); 3.95(s, 3H); 4.09(t, 2H); 4.34(t, 2H); 5.9(s, 2H); 6.3(s, 1H); 7.14(s, 1H); 7.63(s, 1H); 8.17(s, 1H); 8.5(s, 1H) MS-ESI: 456 [MH]+

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; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 52522-99-3, 5-Iodo-2,4-dimethoxypyrimidine, 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, Product Details of 52522-99-3, blongs to pyrimidines compound. Product Details of 52522-99-3

Preparation 70: 5-(2-Chloro-5-fluoro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep70); 5-lodo-2,4-dimethoxy-pyrimidine (868 mg, 3.3 mmol) was dissolved in degassed n-PrOH (30 ml) and then 2-chloro-5-fluoropyridine-3-boronic acid (858 mg, 4.9 mmol), Na2CO3 (700 mg, 6.6 mmol), PPh3 (88 mg, 0.33 mmol) and Pd(OAc)2 (90 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between brine and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether 2-8 affording 240 mg of the title compound (27% yield). MS (ES) (m/z): 270 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52522-99-3, 5-Iodo-2,4-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Glaxo Group Limited; WO2007/113232; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 13544-44-0, 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 13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,4-dichloro-5-iodopyrimidine (5.00 g) synthesized according to the method described in WO2008/155140A1 in tetrahydrofuran (50 mL), N,N-diisopropylethylamine (3.49 mL) and pyrrolidine (1.65 mL) were added under ice cooling, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, 1.0 mol/L aqueous hydrochloric acid was added. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain 2-chloro-5-iodo-4-(pyrrolidin-1-yl)pyrimidine (H1, 4.49 g). [1195] MS m/z (M+H): 310.1

According to the analysis of related databases, 13544-44-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM CORPORATION; TAKASAKI, Masaru; TSUJINO, Toshiaki; TANABE, Shintarou; OOKUBO, Megumi; SATO, Kimihiko; HIRAI, Atsushi; TERADA, Daisuke; INUKI, Shinsuke; MIZUMOTO, Shinsuke; US2015/45339; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 69034-12-4, Adding some certain compound to certain chemical reactions, such as: 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine,molecular formula is C5H2ClF3N2, 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 69034-12-4.

11059] To (±)-tert-butyl 2-hydroxy-7-azabicyclo[2.2. 1] heptane-7-carboxylate (exo) (52 mg, 0.25 mol) in DMF (5 mE) was added 60 wt % NaH (20 g, 0.5 mmol) in one portion. The reaction was heated at 80 C. for 5 mm, then 2-chloro- 5-(trifluoromethyl)pyrimidine (89.7 g, 0.49 mmol) was added. After heating at 80 C. for 2 hours, water was added and the mixture extracted with DCM (3x). The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (0-50% EtOAc in hexanes) gave the title compound (20 g, 23%). MS (ESI) mass calcd. for: C,6H2QF3N303, 359.4; mlz found 260.1 [M-Boc].

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. 69034-12-4, 2-Chloro-5-(trifluoromethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; COATE, Heather R.; DVORAK, Curt A.; FITZGERALD, Anne E.; LEBOLD, Terry P.; PREVILLE, Cathy; SHIREMAN, Brock T.; (473 pag.)US2016/46640; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia