Tag: M.W:100-200

Synthetic Route of 1500-85-2 ,Some common heterocyclic compound, 1500-85-2, molecular formula is C6H6N4, 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.

Solid K2CO3 (0.930 g, 6.71 mmol, 3.0 equiv) was added to a stirringsolution of 7H-pyrrolo[2,3-d]pyrimidin-4-amine 16 (0.300 g,2.24 mmol, 1.0 equiv) in dry DMF (15 mL) at room temperature. After 1 h, a solution of tert-butyl (2-chloroethyl)carbamate (0.602 g,3.35 mmol, 1.5 equiv) in dry DMF (5 mL) was added dropwise. Theresulting suspensionwas stirred for 48 h at 80 C. After the reactionwas complete, as indicated by TLC, the crude material was filteredthrough a plug of Celite to remove inorganic salts and thenwashedwith dichloromethane (50 mL x 4). The filtratewas concentrated byrotary evaporation and purification was carried out using 9%methanol/dichloromethane as the eluent to provide a light brownsolid of the corresponding tert-butyl carbamate. This material wasdissolved in 15 mL of a 1:1 (v/v) mixture of trifluoroacetic acid anddichloromethane. The resulting solution was stirred at room temperaturefor 4 h before it was concentrated by rotary evaporation at35 C. The resulting trifluoroacetic acid salt of the deprotectedamine was dissolved in absolute ethanol (20 mL) and stirred withAmberlyst A-21 free base resin (4 g) at room temperature for 10 h.The heterogeneous reaction mixture was filtered and washed withmethanol (50 mL x 4) until the chromophorewas no longer evidentin the drippingwash by TLC. The filtratewas concentrated by rotaryevaporation and purified using 15% ammonia-saturated methanol/dichloromethane as the eluent to provide product D as a lightbrown solid in 58% yield (0.231 g, 1.30 mmol) from 16. m.p.145e146 C; 1H NMR (DMSO-d6, 500 MHz): d 8.03 (1H, s), 7.14 (1H,d, J 3.4 Hz), 6.90 (2H, br, s), 6.50 (1H, d, J 3.4 Hz), 4.07 (2H, t,J 6.6 Hz), 2.86 (2H, t, J 6.6 Hz), 1.57 (2H, br, s); 13C NMR(DMSO-d6, 125 MHz): d 157.37, 151.40, 149.55, 124.38, 102.35, 98.07,47.16, 41.99; HRMS: m/z calcd for C8H11N5,177.1014; found 177.1010.

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. 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gibbons, Garrett S.; Chakraborty, Amarraj; Grigsby, Sierrah M.; Umeano, Afoma C.; Liao, Chenzhong; Moukha-Chafiq, Omar; Pathak, Vibha; Mathew, Bini; Lee, Young-Tae; Dou, Yali; Schuerer, Stephan C.; Reynolds, Robert C.; Snowden, Timothy S.; Nikolovska-Coleska, Zaneta; European Journal of Medicinal Chemistry; vol. 189; (2020);,
Pyrimidine | C4H4N2 – PubChem,
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Related Products of 62802-42-0, 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 62802-42-0, name is 2-Chloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

4-[4-(5,5-Dimethyl-[1 ,3,2]dioxaborinan-2-yl)-3-fluoro-phenyl]-3,6-dihydro-2H- pyridine-1-carboxylic acid tert-butyl ester (19AB)(1.55g, 3.98 mmol, 1 equiv), 2- Chloro-5-fluoro-pyrimidine (20AB)(634 mg, 591 uL, 4.78 mmol, 1.2 equiv), and 2M sodium carbonate (9.95 ml_) were added in a pressure vessel (350 ml_) and a (1v : 1v) mixture of toluene and ethanol (25 ml_ : 25 ml_) was added. The mixture was then bubbled with nitrogen gas for about 10 minutes. Tetrakis(triphenylphosphine) palladium (0) (462 mg, 0.4 mmol, 0.1 equiv) was added to the mixture. The reaction vessel was tightly capped, placed in an oil bath at 90C, and stirred overnight.The reaction mixture was cooled down to room temperature and diluted with ethyl acetate. The crude mixture was transferred into a seperatory funnel and washed with a (1v : 1v) brine and water mixture. The organic layer was separated and combined and dried over magnesium sulfate. The crude product was then filtered into a flask and the solvent was removed on rotovap. The residue was taken up in as little dichloromethane as possible and purified by column chromatography using Analogix purification system with the following conditions: Solvent A: Dichloromethane; Solvent B: Methanol. Flow Rate: 45 mL/min. Gradient: 0% Solvent B to 10% Solvent B in 60 minutes.Yield= 677 mg (46%)

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 62802-42-0, 2-Chloro-5-fluoropyrimidine.

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
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Electric Literature of 696-82-2, 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. 696-82-2, name is 2,4,6-Trifluoropyrimidine, molecular formula is C4HF3N2, 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) 26.8 parts of 4,6-diaminobenzene-1,3-disulfonic acid (hereinafter referred to as m-bis disulfonic acid) was dissolved in 200 parts of water, With 10% sodium carbonate solution to adjust the pH to 6, the whole solution, and then added 13.5 parts of trifluoropyrimidine at a temperature of 15 C, a pH of 4 under conditions of condensation 4. 0h, bis End point, to obtain a condensation product;

According to the analysis of related databases, 696-82-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Demeike Chemical Co., Ltd.; Wang Xiaojun; (8 pag.)CN106398299; (2017); A;,
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Electric Literature of 5604-46-6, Adding some certain compound to certain chemical reactions, such as: 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde,molecular formula is C5H3Cl2N3O, 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 5604-46-6.

Intermediate 30Ethyl 2-(2-amino-6-chloro-5-formylpyrimidin-4-ylthio)acetate To a stirred suspension of 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (Intermediate 29, 10.66 g, 55.52 mmol) in ethanol (100 mL), triethylamine (8.51 mL, 61.07 mmol) and ethyl 2- mercaptoacetate (6.12 mL, 55.52 mmol) were added. The reaction mixture was stirred at room temperature for 3 h. The precipitate was collected by filtration and washed with water, then recrystallized from 2-propanol, and dried in vacuo to afford 12.6 grams of the title compound. Reference: Tumkevicius, S. et al., J. Heterocyclic Chem., 2006, 43, 1629-33. LC/MS (ES+)[(M+H)+]: 276, 278 for C9Hi0ClN3O3S. 1R NMR (300 MHz, d6-DMSO): 1.19 (t, 3H), 3.98 (s, 2H), 4.10 (q, 2H), 7.95 (s, IH), 8.25 (s, IH), 10.08 (s, IH).

According to the analysis of related databases, 5604-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27732; (2009); A1;,
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Pyrimidine – Wikipedia

Reference of 17321-93-6 ,Some common heterocyclic compound, 17321-93-6, molecular formula is C5H6BrN3, 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-bromo-4-methylpyrimidine-2-ylamine (5.0g, 26 mmol), potassium acetate (7.83g, 79.8 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 1,3,2- dioxaborolane (7.43 g, 29.2 mmol) in dioxane (140 mL) was stirred for 20 min under nitrogen. 1, 1 ‘-bis (diphenylphosphino) ferrocene palladium (II) chloride dichloromethane adduct (1.08 g, 1.33 mmol) was added to the reaction mixture. The reaction mixture was heated to 115 °C for 18 h under nitrogen. Upon completion, the mixture was cooled and EtOAc was added. The resulting mixture was sonicated and filtered. Additional EtOAc was used to wash the solid. The combined organic extracts were washed with water, dried over MgS04, filtered and concentrated. The crude was purified by chromatography eluting with 20-100percent EtO Ac/hex ane to yield 4.5 g of 4-methyl-5-(4,4,5,5-tetramethyl (l,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine (yield: 74percent). 1H-NMR (DMSO, 400 MHz): delta 8.28 (s, 1H), 6.86 (br s, 2H), 2.35 (s, 3 H), 1.25 (s, 12 H). MS (ESI) m/e (M+H+) 236.15, 154.07.

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. 17321-93-6, 2-Amino-5-bromo-4-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing; WO2012/82997; (2012); 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;,
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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

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

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;,
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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;,
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