Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]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, Product Details of 22276-95-5, blongs to pyrimidines compound. Product Details of 22276-95-5

General procedure: N,O-Bis(trimethylsilyl)acetamide (488.2 mg, 586.8 muL, 2.40 mmol) was added to a suspension of 7-bromo-6-chloro-7-deazapurine (464.9 mg, 2.00 mmol) in 20 mL dry acetonitrile. Afterwards, the solution was stirred for 15 min at room temperature in an argon atmosphere,followed by the addition of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-Dribofuranose(1.21 g, 2.40 mmol) and trimethylsilyl trifluoromethanesulfonate(533.4 mg, 434.4 muL, 2.40 mmol). The reaction mixture was heated for 2 h at 80 C under argon with vigorous stirring. After glycosylation, the solution was left to cool down and diluted with 400 mL ethyl acetate. The organic phase was sequentially washed twice with a saturated sodium hydrogen carbonate solution and brine. Subsequently, the organic layer was dried with magnesium sulfate and the solvent was removed under vacuum, to afford the crude nucleoside. Purification by column chromatography on silica gel with hexane/ethylacetate (2:1) as eluent yielded the product as colorless solid (864.0 mg,1.28 mmol, 64%). 1H NMR (300 MHz, DMSO-d6) delta 8.62 (1H, s), 8.32(1H, s), 8.00-7.84 (6H, m), 7.69-7.61 (3H, m), 7.54-7.40 (6H, m), 6.73(1H, d, J=5.0 Hz), 6.32-6.28 (1H, m), 6.16-6.11 (1H, m), 4.90-4.85(1H, m), 4.84-4.65 (2H, m); 13C NMR (75 MHz, DMSO-d6) delta 165.4,164.7, 164.5, 151.4, 151.0, 150.3, 134.0, 133.9, 133.6, 129.4, 129.4,129.3, 129.2, 129.2, 128.8, 128.6, 128.2, 114.9, 88.1, 86.6, 79.3, 73.5,70.6, 63.4; HRMS (ESI): m/z calcd for C32H24BrClN3O7 [M+H]+676.0481, found 676.0489.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Lelle, Marco; Otte, Maik; Thon, Susanne; Bertinetti, Daniela; Herberg, Friedrich W.; Benndorf, Klaus; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1704 – 1713;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5751-20-2, 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. 5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one, molecular formula is C5H6N2OS, 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 11 Synthetic route

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 5751-20-2, 2-(Methylthio)pyrimidin-4(3H)-one.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Changyou; ZOU, Wuxin; HUA, Yuxia; DANG, Qun; WO2011/133444; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 31519-62-7, 2-Pyrimidinecarboxylic acid, 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, 31519-62-7, blongs to pyrimidines compound. COA of Formula: C5H4N2O2

A flask was charged with pyrimidine-2-carboxylic acid (63.2 mg, 0.509 mmol, 1.00 equiv), DCM (5 mL), and thionyl chloride (121 mg, 1.02 mmol, 2.00 equiv). The resulting solution was stirred for 1 h at 40 C. The resulting mixture was concentrated under reduced pressure to provide 72.0 mg (99% yield) of pyrimidine-2-carbonyl chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31519-62-7, its application will become more common.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WEBER, Olivia D.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; JONES, Todd K.; (275 pag.)WO2019/46318; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5305-59-9, Adding some certain compound to certain chemical reactions, such as: 5305-59-9, name is 6-Chloropyrimidin-4-amine,molecular formula is C4H4ClN3, 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 5305-59-9.

General procedure: 2-Amino-4-chloropyrimidine (55) (13.0g, 100mmol) was added to a 57wt.% aqueous solution of hydriodic acid (115ml, 1.00mol) at 0C and the mixture was stirred at room temperature for 3h. The mixture was cooled to 0C and the resulting precipitate was removed by filtration and taken up in cold 5N aqueous Na2CO3 (200ml). The mixture was extracted with EtOAc (3×500ml) and the combined organic layers were concentrated under reduced pressure to deliver 2-amino-4-iodopyrimidine (21.1g, 95.0mmol, 95% yield) as a white solid.

According to the analysis of related databases, 5305-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Reichelt, Andreas; Bailis, Julie M.; Bartberger, Michael D.; Yao, Guomin; Shu, Hong; Kaller, Matthew R.; Allen, John G.; Weidner, Margaret F.; Keegan, Kathleen S.; Dao, Jennifer H.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 364 – 382;,
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. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, 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. category: pyrimidines

General procedure: To a solution of nitrogen-containing nucleophile (1 eq.) and cesium carbonate (3.0 eq.) in N,N-dimethylformamide (2 mL/mmol) was added 2-haloheterocycle (1.1 eq.). Thereaction was heated to 100 C. and stirred at this temperature for 2 hours. Thereaction was then cooled to room temperature and acidified to pH=1 with 10%aqueous HCl solution if product contains a carboxylic acid, or diluted withwater if neutral. The solution was extracted with twice with dichloromethane.The organic layers were combined, dried with sodium sulfate and concentratedunder vacuum. The crude material was either used directly in subsequentreactions or purified by flash chromatography.

With the rapid development of chemical substances, we look forward to future research findings about 6299-85-0.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 24391-41-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, 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, HPLC of Formula: C7H3ClN4, blongs to pyrimidines compound. HPLC of Formula: C7H3ClN4

To a solution of 4-(dimethylamino)cyclohexan-l-ol (320 mg, 2.23 mmol, 3.99 equiv) in tetrahydrofuran (10 mL) was added sodium hydride (360 mg, 9.00 mmol, 26.79 equiv) at 0C. The resulting solution was stirred for 30 min at 0C. Then 4-chloro-7H-pyrrolo[2,3- d]pyrimidine-5-carbonitrile (100 mg, 0.56 mmol, 1.00 equiv) was added. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at reflux. The reaction was then quenched by the addition of 2 mL of water. The resulting mixture was concentrated under vacuum. The crude product (80 mg) was purified by Prep-HPLC with the following conditions: Column, Xbridge Prep C 18 5um, 19x150mm; mobile phase, water with 50mL HCOOH and CH3CN (5.0% CH3CN up to 42.0% in 10 min, up to 95.0% in 2 min, down to 5.0%) in 2 min); Detector, 220/254nm. 30.2 mg product was obtained. This resulted in 30.2 mg (19%) of 4-[[4-(dimethylamino)cyclohexyl]oxy]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile as a brown solid. LC-MS:(ES,m/z): 286 [M+H]+ 1H NMR (300 MHz, DMSO, ppm): 51.18-1.55 (m, 4H), 1.86-1.89 (d, 2H), 2.13-2.17 (d, 2H), 2.17 (s, 6H), 2.39 (m, 1H),5.15-5.20 (m, 1H), 8.22- 8.26 (m, 2H), 8.43 (s, 1H).

The synthetic route of 24391-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS IRIS, INC.; HARRIMAN, Geraldine C.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; WESSEL, Matthew David; GREENWOOD, Jeremy Robert; WO2014/11911; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 213265-83-9 ,Some common heterocyclic compound, 213265-83-9, molecular formula is C4HCl2FN2, 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.

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 trans-2, 6-DIMETHYLHEXAHYDRO-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 0.31 g of 1- (6-CHLORO- 5-fluoropyrimidin-4-yl) -trans-2, 6-DIMETHYLHEXAHYDRO-LH-AZEPI ne. 1H-NMR : 0.92 (d, 3H), 1.19 (d, 3H) 1.44-1. 65 (m, 5H), 1.94-2. 11 (m, 2H), 3.41 (d, 1H), 4.17 (brd, 1H), 4.47-4. 56 (m, 1H) 8.10 (d, 1H)

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. 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

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

Reference of 37538-67-3, 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 37538-67-3, name is Pyrido[3,2-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Potassium hydride (KH, 30% in mineral oil, 4.0 g) was suspended in 50 mL of dimethylformamide (DMF). It was cooled in an ice-water bath, and solid 3H-quinazolin-4-one (4.3 g) was added in. After 30 min, a solution of oxirane 14 (3.5 g) in 10 mL of DMF was added in. The reaction mixture was then heated at 80 C for 8 h under nitrogen atmosphere. It was partitioned between ethyl acetate (75 mL) and water (75 mL), separated organic layer was washed with water (3 × 50 mL), then brine (50 mL), dried over anhydrous sodium sulfate, and evaporated in a rotary evaporator under reduced pressure to furnish the crude product. Silica gel flash chromatography (75% ethyl acetate in hexanes) furnished 15 as off white solid. Yield: 79%.

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 37538-67-3, Pyrido[3,2-d]pyrimidin-4(3H)-one.

Reference:
Article; Zhu, Shuren; Chandrashekar, Gudise; Meng, Li; Robinson, Katie; Chatterji, Dipsanker; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 927 – 932;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, 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, 171887-03-9, blongs to pyrimidines compound. Application In Synthesis of N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide

To a slurry of N-(2-amino-4,6-dichloro-5-pyrimidinyl) formamide (70 gm) in ethanol (700 ml), pulverized sodium bicarbonate (56.80 g) was added at -230C and heated to 75-8O0C. A solution of 4-amino-2-hydroxymethylbutan-l-ol (45 gm, -95% purity) in a mixture of ethanol (200 ml) and water (20 ml) was slowly added to the refluxing reaction mass in -60 minutes. The mixture was stirred at 75-8O0C for 90 minutes and cooled to -230C. The precipitated salts (~45g) were filtered off and then washed with ethanol (100ml). The filtrate and washings were combined and treated with activated charcoal (3 g). The solution was filtered through celite to remove carbon and the residue washed with ethanol (40 ml). To the filtrate, triethylamine (38 g) and 10% palladium on carbon (50% water paste, 10 g) were added. The slurry was transferred to an autoclave and hydrogenated at 5O0C and 5-6 kg/cm2 for 18 hrs. After completion of the reaction, the catalyst was removed by filtration and the residue was washed with ethanol (50 ml). The combined filtrate (~1150 ml) was concentrated to -300 ml under reduced pressure at <60C. The concentrate was cooled to 230C and a solution of hydrogen chloride in ethanol (118 gm, 15% w/w) was added to the reaction mass. The resulting light yellow coloured reaction mass was stirred for 5-10 minutes and triethylorthoformate (23Og) was added. The reaction solution was heated to 45- 5O0C and continued stirring at 45-5O0C for 3 hrs. Thereafter a mixture of 6.4g concentrated hydrochloric acid and 9.6 g water was added. Stirring was continued at 45-5O0C for 90 minutes, to crystallize the product. The suspension was cooled to 15-180C, stirred for 60 minutes and the product was filtered. The wet product was washed with ethanol (2 x 50ml, 250C), and dried at 5O0C under reduced pressure to constant weight. (Yield 50.5 gm; light yellow powder, HPLC purity >97%.)This product can be taken as such for famciclovir preparation or can be purified by a process described below:The above obtained product (50.5 gm) was suspended in a mixture of ethanol (220 ml) and water (7 ml) and the slurry was refluxed for 30-40 minutes. Thereafter, cooled the mass to 8-1O0C and maintained for 1 hr. Product was filtered, washed with ethanol (60 ml), and dried at 5O0C under reduced pressure to constant weight. (Yield 43.8gm; off white powder, HPLC purity > 99.3 %.)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,171887-03-9, its application will become more common.

Reference:
Patent; AUROBINDO PHARMA LIMITED; WO2008/72074; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3435-28-7, 6-Methylpyrimidin-4-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, 3435-28-7, blongs to pyrimidines compound. Application In Synthesis of 6-Methylpyrimidin-4-amine

A mixture of 2-(4-bromo-7-fluorothiazolo[5,4-c]pyridin-2-yl)-3-chlorobenzonitrile (0.110 g, 0.30 mmol), 6- methylpyrimidin-4-ylamine (35 mg, 0.32 mmol), XantPhos (0.018 g, 0.03 mmol) and Cs2C03 (247 mg, 0.75 mmol) in dioxane (2.5 mL) was degassed with a stream of argon. Pd2(dba)3 (0.014 g, 0.015 mmol) was added and the reaction mixture was heated at 80 C for 2 hours in a sealed vial. After cooling to room temperature, the crude reaction mixture was filtered through Celite washing with EtOAc (50 mL). The filtrate was concentrated to dryness under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-100% EtOAc in DCM, then triturated with diethyl ether (x 2), to afford the title compound as a pale yellow solid (43 mg, 36% yield). NMR (400 MHz, CDC13): delta 8.73 (d, J = 1.2 Hz, 1H), 8.34 (d, J = 1.8 Hz, 1H), 7.86-7.76 (m, 3H), 7.66 (t, J = 8.0 Hz, 1H), 7.57 (br s, 1H), 2.56 (s, 3H). LCMS (Method C): RT = 3.31 min, m/z: 397 [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,3435-28-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia