Month: November 2020

1500-85-2, A common compound: 1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine,molecular formula is C6H6N4, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: Procedure G: To a solution of 7H-pyrrolo[2,3-d]pyrimidin-4-amine (1, 0.32 g, 2.39 mmol) and 2?-chloro-4?-methylspiro[cyclohexane-1,7?-pyrrolo[3,4-b]pyridin]-5?(6?H)-one (2, 0.6 g, 2.39 mmol) in 1,4-dioxane (15 mL) was added cesium carbonate (2.33 g, 7.17 mmol). The reaction mixture was purged with argon for 5 min. and then XanthPhos (69 mg, 0.11 mmol), XPhos (57 mg, 0.11 mmol), tris(dibenzylideneacetone)dipalladium(0) (109 mg, 0.11 mmol) and palladium acetate (27 mg, 0.11 mmol) were added and the reaction mixture purged for an additional 5 min. The purged reaction mixture was stirred at 100 C. for 4 h. After TLC showed completion, the reaction mixture was filtered through a bed of celite and the resulting filtrate was concentrated. The crude product was purified by preparative HPLC. The desired fractions were concentrated to dryness under vacuum to afford 2?-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4?-methylspiro[cyclohexane-1,7?-pyrrolo[3,4-b]pyridin]-5?(6?H)-one as a yellow solid. Yield: 0.095 g, 11%;

With the rapid development of chemical substances, we look forward to future research findings about 1500-85-2.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); 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.5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, molecular formula is C8H9ClN2O2S, molecular weight is 232.6873, as common compound, the synthetic route is as follows.5909-24-0

[4-C hlor o-2-(methylthio)pyrimidin-5-yl] methanol. 4-Chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (62 g, 260 mmol) was dissolved in anhydrous tetrahydrofuran (500 mL) in a 3-necked 5L round bottomed flask fitted with a mechanical stirrer, addition funnel, temperature probe and nitrogen inlet. The solution was cooled to 0C. Diisobutylaluminum hydride in tetrahydrofuran (1M solution, 800 mL) was added dropwise over a period of 2 hours. After the addition was complete, the reaction mixture was kept at 0C for 0.5 hours. The reaction was quenched at 0C by the slow addition of saturated aqueous sodium sulfate (265.3 mL, 530.7 mmol) keeping the internal reaction temperature below 10C. Ethyl acetate (900 mL) was added and the reaction slowly warmed to room temperature overnight. 6M HC1 was added till the reaction mixture was slightly acidic (pH 6). The reaction mixture was filtered thru a pad of Celite and the aluminum salts were washed with ethyl acetate (1L). The filtrate was poured into a separatory funnel and washed twice with water (600 mL) and finally with brine (600 mL). The organic layer was dried over sodium sulfate, filtered thru Celite and the solvent concentrated in vacuo to afford 39.2g (77% crude yield) of a dark yellow oil. The material was used as is for the next step. NMR (CDCI3) delta 8.56 (s, 1H), 4.76 (s, 2H), 2.59 (s, 3H); MS (ESI+) for C6H7C1N20S m/z 191.0 (M+H)+ .

Statistics shows that 5909-24-0 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; BISI, John, Emerson; ROBERTS, Patrick, Joseph; GASTON, Ricky, D.; GADWOOD, Robert, C.; WO2015/161287; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A common compound: 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine,molecular formula is C4HCl2FN2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 213265-83-9

Into 3 ml of acetnitrile were added 0.2 g of 4, 6-DICHLORO-5-FLUOROPYRIMIDINE, 0.50 g of pottasium carbonate and 0.27 g of cis-2, 6-DLMETHYLHEXAHYDRO-LH-AZEPINE hydrochloride, and the mixture was stirred for 2 hours at 60 C. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.3 g of 1- (6-CHLORO- 5-fluoropyrimidin-4-yl) -cis-2, 6-DIMETHYLHEXAHYDRO-LH-AZEPINE H-NMR : 0.90-1. 04 (m, 4H involving a doublet at 0.95), 1.10-1. 32 (m, 4H), 1.36-1. 48 (m, 1H), 1.71-1. 90 (m, 3H), 2.04-2. 14 (M, 1H), 2.91 (brt, 1H), 3.70 (brs, 1H), 4.42-4. 82 (br, 1H) 8.09 (d, 1H) GC-MS: 257 (M+)

With the rapid development of chemical substances, we look forward to future research findings about 213265-83-9.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2004/99160; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide. This compound has unique chemical properties. The synthetic route is as follows. 147118-37-4

Methyl magnesium chloride solution (3M) (11.87 ml, 0.0356 moles) in tetrahydrofuran was added to a pre-cooled suspension of pyrimidine carboxaldehyde (5 g, 0.0142 moles) in anhydrous tetrahydrofuran (30 ml) under stirring for 30 min at 0-5 C. The reaction mass was stirred at the same temperature. After completion of the reaction, the reaction mass was poured into pre-cooled saturated ammonium chloride solution (100 ml) at 0-5 C. and stirred for 1 h at 5-10 C. The product was extracted into ethyl acetate (150 ml) and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was distilled under vacuum at 40-45 C. until the traces of ethyl acetate were completely removed to give the title compound.

Statistics shows that 147118-37-4 is playing an increasingly important role. we look forward to future research findings about N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide.

Reference:
Patent; Mallela, Sambhu Prasad Sarma; Nandi, Sakumar; Nangi, Gangadhara Bhima Shankar; Ananta, Rani; Meenakshiunderam, Sivakumaran; US2011/178296; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

90213-66-4, 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. 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3Cl2N3, 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 2,4-dichloro-7H-pyrrolo[2,3-djpyrimidine 34 (237 mg, 1.26 mmol) in CH3CN (1 mL) was added NaH (33.3 mg, 1.39 mmol) portion- wise at 0 C. The reaction mixture was stirred at room temperature for 20 mm until gas evolution was ceased. Methyl iodide (86.4 i.il, 1.39 mmol) was added and stirred the reaction mixture for 1 h at room temperature. To the reaction mixture was added water and extracted with ethyl acetate (2 x 30 mL). The combined organic layers were dried over Mg504, and then concentrated under vacuum. The resultant crude residue was purified by silica-gel column chromatography to afford 35 (144 mg, 58%) as white solid. ?H-NMR (400 MHz, DMSO-d6) oe 7.76 (d, J = 3.6 Hz, 1H), 6.71 (d, J = 3.6 Hz, 1H), 3.81 (s, 3H); MS: (m/z) [M+Hjb 204.02.

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. 90213-66-4, 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING / MCGILL UNIVERSITY; TSANTRIZOS, Youla S.; SEBAG, Michael; (120 pag.)WO2018/137036; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

156-83-2, 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. 156-83-2, name is 6-Chloropyrimidine-2,4-diamine, molecular formula is C4H5ClN4, 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 NaH (2.77 g, 69.2 mmol) in ethanol (150 ml) was added 2,6-diamino-4-chloropyrimidine (5.0 g, 34.6 mmol). The mixture was refluxed for 6 h. After cooling, the solution was neutralized with a 5-6 N HCl solution in isopropyl alcohol. After removing the solvents in vacuo, the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 40:1), yielding the title compound as a white solid (4.0 g, 75%). Mp 164-165 C. 1H NMR (300 MHz, DMSO, 25 C): delta = 6.00 (s, 2H, NH2), 5.88 (s, 2H, NH2), 5.03 (s, 1H, CH), 4.13 (q, J = 7.1 Hz, 2H, CH2), 1.22 (t, J = 7.1 Hz, 3H, CH3) ppm. 13C NMR (75 MHz, DMSO, 25 C): delta = 170.0, 165.9, 162.9, 76.1, 60.2, 14.7 ppm. HRMS: calcd for C6H11N4O [M+H]+ 155.09329, found 155.09260.

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. 156-83-2, 6-Chloropyrimidine-2,4-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jang, Mi-Yeon; Jonghe, Steven De; Segers, Kenneth; Anne, Jozef; Herdewijn, Piet; Bioorganic and Medicinal Chemistry; vol. 19; 1; (2011); p. 702 – 714;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

109-12-6, 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. 109-12-6, name is Pyrimidin-2-amine, the common compound, a new synthetic route is introduced below.

General procedure: 0.5 mol% ruthenium(II) catalyst was stirred with 4 mmol ofKOH in toluene. To this mixture, 2 mmol of alcohol and 2 mmolof amine were added and the temperature was raised up to120 C. The progress of the reactions was monitored using TLC.As soon as the reaction was completed, the mixture was cooledto room temperature and added 3 mL of distilled water. The combinedmixture was extracted with CH2Cl2 and dried by addingmagnesium sulfate. The crude product was purified by columnchromatography (n-hexane/EtOAc) and characterized by 1H NMRspectral analyses. The 1H NMR data obtained for the catalytic productswere compared with literature [19].

Statistics shows that 109-12-6 is playing an increasingly important role. we look forward to future research findings about Pyrimidin-2-amine.

Reference:
Article; Prakash, Govindan; Ramachandran, Rangasamy; Nirmala, Muthukumaran; Viswanathamurthi, Periasamy; Sanmartin, Jesus; Inorganica Chimica Acta; vol. 427; (2015); p. 203 – 210;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1780-26-3, 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 1780-26-3 as follows.

Into clean and dry 5.0 L 4-neck RB flask charged 2-amino-N-(2-chloro-6-methyl (0125) phenyl)-5-thiazole-l-carboxamide (200gm), 4,6-dichloro-2-methyl (0126) pyrimidine(146 g), 2.0 L of THF under nitrogen atmosphere. Clear solution (0127) formation was observed, cooled the reaction mass to temperature 10-20C, added (0128) 30% sodium -t-butoxide (845gm) solution to the reaction mass over a period of 60- (0129) 75min at temperature 10-20C. Brown coloured solution formation was observed. (0130) Reaction mass temperature was raised to 25-30C and maintained the reaction (0131) mass temperature to 25-30C for 90-120 min, cooled the mass to temperature 0- (0132) 5C and added 2N HCl solution to the reaction mass over a period of 60-90min at 0-5C and maintained for 105-120min. Transferred the reaction mass into a buchner funnel and flask kept under plant vacuum. Washed the wet cake with 600.0mlof water.Suck dried thoroughly for 45-60 mi and dried the wet material in a drier at temperature 60-65 C for 8-10hrs. (0133) Weight: 210 gm

The chemical industry reduces the impact on the environment during synthesis 1780-26-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NATCO PHARMA LIMITED; KONAKANCHI, Durga Prasad; GONGALLA, Buchappa; KOTRA, Uma Naresh Babu; SAKKANI, Srinivasulu; RAGIDI, Dharmender; SIKHA, Kotayyababu; NANNAPANENI, Venkaiah Chowdary; (18 pag.)WO2018/100585; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

109-12-6, 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. 109-12-6, name is Pyrimidin-2-amine, molecular formula is C4H5N3, 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), weighing 1.008g 2-amino pyrimidine (10.6mmol), 1.480g chloro acetyl chloride (13.1mmol), 1.779g potassium carbonate (12.9mmol) and 13 ml dichloromethane;(2), will step one (1) weighed in 2-amino pyrimidine, potassium carbonate and two-thirds the volume of dichloromethane (about 9 ml) with nitrogen protection device is of the three-port flask, in 0 C under the condition of stirring to dissolve;(3), will step one (1) weighed chloroacetic chloride in and the remaining dichloromethane (about 4 ml) in the constant voltage dropping funnel, then with a constant acceleration of 0.25 ml/min into the three-port flask, 20 min the completion of the dropping, the continued after dropping 0 C stirring reaction under the conditions of 3h, obtaining a reaction product;(4), using vacuum filtration device, step a (3) in the obtained after filtering the reaction product is the reaction product of in addition to the solvent, each with 10 ml deionized water washing the product, washing a total of 5 times, at a temperature of 45 C the product under the conditions of drying, drying time is 5h, the lime-green powdery solid, lime-green powdery solid is acetyl-2-amino pyrimidine, weighing mass is 1.550g, yield 85.22%.

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. 109-12-6, Pyrimidin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Qiqihar University; Wang, Liyan; Liu, Shifu; Tian, Ying; He, Xianyou; Zhang, Hui; (10 pag.)CN105906572; (2016); 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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide. A new synthetic method of this compound is introduced below., 147118-37-4

EXAMPLES Preparation of rosuvastatin (+)- (3R, 5S)-7- [4- (4-FLUOROPHENYL)-6-ISOPROPYL-2- (N-METHYL-N-METHANESULFONYLAMINO) PYRIMIDIN-5-YL]-3, 5-DIHYDROXY-6 (E) -heptenoic acid calcium salt (2: 1). EXAMPLE 1 Step A Preparation of condensed product N- [5- [- (TERT-BUTYL-DIMETHYL-SILANYLOXY)-6- CYANO-3-OXO-HEX-1-ENYL]-4- (4-FLUOROPHENYL)-6-ISOPROPYL-PYRIMIDIN-2-YL]-N- METHYL-METHANESULFONAMIDE (Condensed product, Formula IV) To a solution of pyrimidine aldehyde (1. 0GM) of Formula III in toluene (20MOI), 1-cyano (2S)-2-[(TERT-BUTYIDIMETHYLSILYL) OXY]-5-OXO-6-TRIPHENYLPHOSPHANYLIDENE hexanenitrile of formula 11 was added and the reaction mixture was REFLUXED for about 24 hours. The reaction mixture was concentrated and the residue titurated with cyclohexane (50ML). The cyclohexane layer was concentrated to give a residue which was purified by silica gel chromatography, eluted with toluene to obtain 1.60gm of the condensed product as a thick oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147118-37-4, N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2004/52867; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia