Day: June 25, 2021

Adding a certain compound to certain chemical reactions, such as: 29274-24-6, 5-Chloropyrazolo[1,5-a]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, 29274-24-6, blongs to pyrimidines compound. Application In Synthesis of 5-Chloropyrazolo[1,5-a]pyrimidine

5-Chloropyrazolo[l,5-a]pyri midine (500mg, 3.25mmol) taken up in 3ml acetonitrile and 1.5ml water. 2-isopropoxy-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (lg, 3.9m mol), Potassiu m carbonate (902mg, 6.5m mol), and Pd(dppf)Cl2:DCM (267mg, 0.325m mol) added and reaction stirred in microwave in a sealed tube at 120 C for 12 minutes. Reaction cooled filtered through celite washed through with ethyl acetate and reduced in vacuo. Reaction taken up in 1:1 ethyl acetate: hexane and filtered through a plug of celite. The filtrate was ollected, dried in vacuo to obtain 740 mg of crude product to be used as is in next step. LRMS (ESI) m/z 255 [(M+H)]+, calc’d for C14H14N4O: 254.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29274-24-6, its application will become more common.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; GARDYAN, Michael Walter; GREEN, Michael Green; KUMI, Godwin; ZHANG, Yulian; WO2015/35117; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 54660-78-5, 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.54660-78-5, name is 4-Chloropyrimidin-5-amine, molecular formula is C4H4ClN3, molecular weight is 129.5477, as common compound, the synthetic route is as follows.

Step 1 : To a 50mL round -bottom flask was added 20mL 1, 4-Dioxane, compound 5a (885mg, 6.83mmol, l .Oeq), compound lb (1.61g, 7.52mmol, l. leq) and DIPEA (1.32g, 10.25mmol, 1.5eq). The reaction was heated to reflux for 18h. TLC (PE: EA= 1 : 1) showed the reaction was completed. The reaction mixture was concentrated in vacuum and purified by column chromatography on silica gel eluted with PE: EA= 3 : 1- 1 : 1 to afford the title compound 5b (1.5g, HPLC: 93%, Yield: 71.4%) as an orange solid.

The chemical industry reduces the impact on the environment during synthesis 54660-78-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LIANG, Congxin; (62 pag.)WO2018/5713; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 24415-66-5, 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.24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, molecular weight is 168.58, as common compound, the synthetic route is as follows.

Example 56[0486]5-Methyl-N- {1- [4- (trifluoromethyl) phenyl] cyclopropyl} [1, 2, 4] triazolo [1, 5-a] pyrimidin-7-amine[0487][0488]Step 1: 5-Methyl-N- {1- [4- (trifluoromethyl) phenyl] cyclopropyl} [1, 2, 4] triazolo [1, 5-a] pyrimidin-7-amine[0489][0490]To a solution of commercially available 7-chloro-5-methyl- [1, 2, 4] -triazolo [1, 5-a] pyrimidine (25 mg, 0.148 mmol) and 1- [4- (trifluoromethyl) phenyl] cyclopropanamine hydrochloride (45.5 mg, 0.178 mmol) in anhydrous NMP (0.5 mL) in a 2-5 mL microwave vial was added dropwise via syringe DIEA (0.2 mL, 1.145 mmol) and the resulting solution heated via oil bath to 120 overnight. The reaction was allowed to cool and was quenched with 1 mL of sat’ d sodium bicarbonate soln. The solution was diluted with 5 mL ethyl acetate. The organic layer was separated, the aqueous was re-extracted with 2.5 mL of ethyl acetate and the organics then combined. The organics were washed with 1 mL water, dried over sodium sulfate, filtered and the filtrate concentrated to dryness. The residue was purified by reverse phase HPLC (10-90acetonitrile in water with 0.05TFA) to afford the product as a white fluffy solid. LC-MS (+ESI) m/z 334.1HNMR(500 MHz, CD3OD) delta: 8.56 (s, 1H) , 7.62 (d, J 8.6 Hz, 2H) , 7.44 (d, J 8.6 Hz, 2H) , 6.40 (s, 1H) , 5.17 (q, J 6.8 Hz, 1H) , 2.52 (s, 3 H) , 1.71-1.66 (m, 2H) , 1.64-1.61 (m, 2H) .

Statistics shows that 24415-66-5 is playing an increasingly important role. we look forward to future research findings about 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori J.; CHANG, Lehua; FOSTER, Ashley; CHEN, Yili; DWYER, Michael; GUO, Zack Zhiqiang; WANG, Ming; XU, Shimin; BO, Yingjian; FU, Jianmin; (250 pag.)WO2017/277; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, 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, Formula: C7H9Cl2N3S, blongs to pyrimidines compound. Formula: C7H9Cl2N3S

Example 6 Synthesis of 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl]amino]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]ethanol (Compound I) Take 250mL reaction flask 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (16.1g, 68mmol), 2-[[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-yl]oxy]-1-ethanol (14.8g, 68mmol), triethylamine (68.7g, 680mmol) and n-butanol (100mL) were added at atmospheric pressure. The resulting reaction mixture was sealed and heated to 100C, reflux for 55h. Followed by cooling to 30C. The solvent was distilled off. Isopropyl acetate and water, the phases were separated. The aqueous phase was extracted with isopropyl acetate, the combined organic phases, washed. Dried over anhydrous magnesium sulfate. Filter. The solvent was distilled off, give a reddish brown oil. N-heptane was added after a beating, white solid 24.9g, yield 87.2%. HPLC purity was 99.4%.

The synthetic route of 145783-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qingdao Huanghai Pharmaceutical Co., Ltd.; Zhang, Fuli; Xu, Jianguo; Liu, Xiaohua; Gao, Yongji; He, Xiaoqing; Xu, Taizhi; Hu, Jie; (12 pag.)CN103626745; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 874-14-6, 1,3-Dimethyluracil, 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, Recommanded Product: 1,3-Dimethyluracil, blongs to pyrimidines compound. Recommanded Product: 1,3-Dimethyluracil

General procedure: An 8 mL oven-dried scintillation vial equipped with a magnetic stir bar was charged with a mixture of 4-quinolone or uracil (0.50 mmol, 1.0 equiv), disulfide or thiol (0.75 mmol, 1.5 equiv), molecular iodine (I2) (128 mg, 0.50 mmol, 1.0 equiv), K2S2O8 (1.00-1.50 mmol, 2.0-3.0 equiv), and acetonitrile (CH3CN) (1 mL). The vial was capped, and the reaction mixture was stirred at 60 or 80 C for 12-16 h. Upon completion, saturated Na2S2O3 (5 mL) and distilled deionized H2O (10 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by SiO2 column chromatography to afford the desired thioether products.

The synthetic route of 874-14-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Beukeaw, Danupat; Noikham, Medena; Yotphan, Sirilata; Tetrahedron; vol. 75; 39; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 4994-86-9, 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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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.

A solution of 4-chloro-2-methylpyrimidine (0.050 g, 0.389 mmol), 5-(5- bromo-2-fluoropyridin-3-yl)oxazole (0.100 g, 0.389 mmol) and hexamethylditin (0.097 mL, 0.467 mmol) in 1,4-dioxane (0.1 mL) was purged with argon for 15 min and tetrakis(triphenylphosphine)palladium (0) (0.045 g, 0.039 mmol) was added. The reaction mixture was again purged with argon for 5 min and heated in a microwave for 1 h at 110C. The reaction mixture was diluted with ethyl acetate (8 mL) and water (5 mL) and the organic layer separated. The aqueous layer was extracted again with ethyl acetate (2×5 mL). The combined ethyl acetate layers were washed with brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The reaction mixture was purified by Preparative TLC (70% ethyl acetate in hexanes). The required spot was collected, dissolved 5% methanol in dichloromethane (30 mL), filtered and concentrated under reduced pressure to afford 5-(2-fluoro-5-(2-methylpyrimidin-4-yl)pyridin-3-yl)oxazole (0.070 g, 0.098 mmol, 25% yield) as an off-white solid. LCMS (ESI) m/e 257.0 [(M+H) +, calcd for C13H10FN4O, 257.1]; LC/MS retention time (method B): /R = 0.86 min.

According to the analysis of related databases, 4994-86-9, the application of this compound in the production field has become more and more popular.

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; (485 pag.)WO2017/59085; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4994-86-9, 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 4994-86-9 as follows.

To a solution of N-((rac)-8-endo-3-benzyl-3-azabicyclo[3.2.1]octan-8-yl)-8-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (70 mg, 157 mumol) in methanol (1.6 mL) was added one drop of 25% aqueous hydrogen chloride solution under an atmosphere of nitrogen and stirring. The reaction was hydrogenated over night at 1 bar. The catalyst was filtered off and washed with ethanol. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (1.6 mL). Triethylamine (47.7 mg, 65.7 muL, 471 mumol) and 4-chloro-2-methylpyrimidine (25.0 mg, 189 mumol) were added and the reaction was heated to 150 C. for 30 minutes in a microwave oven. The solvent was removed under reduced pressure after cooling to room temperature and the residue was purified by column chromatography on silica gel using a gradient from ethyl acetate to ethyl acetate/methanol (v/v 9:1) as eluent. The title compound was obtained as a light yellow solid (36 mg, 51%).MS ISP (m/e): 448.5 (100) [(M+H)+], 225.0 (80).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4994-86-9, its application will become more common.

Reference:
Patent; Baumann, Karlheinz; Green, Luke; Limberg, Anja; Luebbers, Thomas; Thomas, Andrew; US2012/225884; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 10070-92-5, 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 10070-92-5 as follows.

Step 1 : Pyrimidin-5-ylmethanolPyrimidine-5-carboxaldehyde (14.97 g, 138 mmol) in methanol (80 mL) at 0 0C was treated portionwise with sodium borohydride (5.24 g, 138 mmol). When the addition of sodium borohydride was complete the mixture was stirred for 1 hour at 0 0C. The mixture was quenched carefully with acetone and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 4OM, eluting with 5% methanol in dichloromethane to give pyrimidin-5-ylmethanol as a white crystalline solid.1H NMR (CDCl3): delta 9.18 (s, 1 H), 8.78 (s, 2 H), 4.81 (s, 2 H) MS: m/e 111.04 (M + H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10070-92-5, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); 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. 16357-83-8, name is 4-Aminopyrimidine-5-carbaldehyde, molecular formula is C5H5N3O, 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. Formula: C5H5N3O

General procedure: To a soln. of aldehyde C-3 (1 eq) and amine BB-9 (1 eq) in THF (4 mL/mmol) were added AcOH (2 eq) and the rxn mixture was stirred for 20 min at RT. NaBH(OAc)3 (4 eq) was added portionwise and the rxn mixture was stirred at RT for a given time (see Table 34). When necessary to reach the complete reduction of the intermediate imine, NaBm (1.2 eq) can be added at 0C and the rxn mixture stirred at RT. It was quenched with a 1 M aq. soln. of NaOH and extracted with EtOAc (3x). The combined org. phases were washed with brine, dried over MgSC>4 and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc/MeOH.

With the rapid development of chemical substances, we look forward to future research findings about 16357-83-8.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (97 pag.)WO2019/141808; (2019); A1;,
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. 1044145-59-6, name is (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H7ClN2OS

General Procedure 5-2: 4-Chloro-2-(methylthio)pyrimidine-5-carbaldehyde[00195] A mixture of (4-chloro-2-(methylthio)pyrimidin-5-yl) methanol (9.0 g, 47 mmol) and activated MnO2 (70 g, 800 mmol, Aldrich Cat. No. 217646) in 120 mL CH2Cl2 was stirred at the room temperature for 24 hours. The mixture was filtered through Celite (Acros Celite 521, Cat.No. 206350010). The filter cake was washed with CH2Cl2 until no UV-active material was seen. The combined CH2Cl2 solution was concentrated and passed through a thin silica gel plug, using 25% EtOAc/Hexanes. The filtrate was concentrated to give an off white solid (6.37 g,71.6% yield).HPLC Rt: 5.53 min.1H-NMR (CDCl3): delta 10.32 (s, IH), 8.88 (s, IH), 2.65 (s, 3H).

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, 1044145-59-6, (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol.

Reference:
Patent; BIOGEN IDEC MA INC.; WO2008/94575; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia