Category: pyrimidines

Adding a certain compound to certain chemical reactions, such as: 5466-43-3, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[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, 5466-43-3, blongs to pyrimidines compound. Quality Control of 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine

EXAMPLE 314; 5-Bromo-3-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-1,3-dihydro-indol-2-one; To a stirring mixture of NaH (480 mg, 12.0 mmol) in THF (20 mL) at 0 C. was added 5-bromooxindole (1.00 g, 4.72 mmol) in portion. Additional THF (5 mL×3) was used to make sure all the oxindole was added into the reaction flask. After stirred for 50 min, a solution of compound 313 (892 mg, 4.72 mmol) in THF (5 mL×3) was added. The reaction was continued stir for 1 h at 0 C. and 2.5 h at room temp. A saturated NH4Cl solution (50 mL) was added into the reaction and the mixture was extracted with EtOAc (50 mL×3). The combined organic extracts was washed with brine and concentrated. The residue was triturated with MeOH and dried to give 1.27 g (74%) the title Example 314. Example 314: 1H NMR (400 MHz, DMSO-d6) delta 10.83 (s, 1H), 7.43 (m, 1H), 7.27 (s, 1H), 6.87 (m, 1H), 5.11 (s, 1H), 3.02-2.76 (m, 4H), 2.13-2.03 (m, 2H); MS (m/e) 365 (M+1), 366 (M+2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Patent; Cephalon, Inc.; US2007/281949; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 444731-75-3 ,Some common heterocyclic compound, 444731-75-3, molecular formula is C14H14ClN5, 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.

To a stirred suspension of Intermediate Example 4 (1.1 g, 3.8 mmol) in 14 ml. of MeOH, was added 5-amino-2-methylbenzenesulfonamide (0.78 g, 4.2 mmol, 1.1 equiv) at room temperature. The reaction mixture was heated at reflux for 3 h, then 4 M HCI in 1 ,4-dioxane (19 mul_, 0.076 mmol) was added in one portion. After 4 h, the suspension was cooled to room temperature, and filtered. The resulting solid was washed with 10 ml. of MeOH and dried in vacuo to yield 1.3 g (72%) of 5-({4-[(2,3-dimethyl-2H-indazol- 6-yl)methylamino]-2-pyrimidinyl}amino)-2-methyl benzenesulfonamide monohydrochloride as a white solid. 1 H NMR (DMSO-d6, 400 MHz) delta 10.95 (s, 1 H), 8.36 (s, 1 H), 7.86 (d, J = 8.8 Hz, 2H), 7.64-7.59 (m, 2H), 7.40 (m, 3H), 6.93 (dd, J = 8.8, 2.0 Hz, 1 H), 5.92 (s, 1 H), 4.08 (s, 3H), 3.57 (s, 3H), 2.65 (s, 3H), 2.56 (s, 3H).

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. 444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143483; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 720-01-4, Adding some certain compound to certain chemical reactions, such as: 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate,molecular formula is C8H6ClF3N2O2, 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 720-01-4.

4-chloro-2- (trifluoromethyl) pyrimidine-5-carboxylate (1.99g, 7.82mmol) solution of ethanol (30 mL) added diisopropyl ethyl amine (2.43g, 18.8mmol), 10% palladium – carbon (200mg), under hydrogen atmosphere, stirred at room temperature for 3.5 hours. Thereafter, the reaction mixture was diatomaceous earth filtration, concentrated under reduced pressure. Utilizing silica column chromatography (hexane / ethyl acetate) The residue obtained was purified, thereby obtaining the title compound (1.36g79%)

According to the analysis of related databases, 720-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA CO., LTD.; YOSHINAGA, HIDEFUMI; URUNO, YOSHIHARU; SAWAMURA, KIYOTO; GOTO, NANA; IKUMA, YOHEI; (165 pag.)TW2016/5858; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
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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 110100-00-0, name is 1-(2-Chloropyrimidin-5-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H5ClN2O

To a stirred solution of Intermediate 16 (1.14 g, 4.24 mmol) in dry DMF (10 mL), TEA (1.1 mL, 16.5 mmol) and 1-(2-chloropyrimidin-5-yl)ethan-1-one obtained in the previous step (0.6 g, 3.85 mmol) were added at rt. The resulting mixture was heated to 90 C for 12 h. It was cooled to rt and concentrated. Dichloromethane (50 mL) was added and was washed with a saturated NaCI solution (10 mL), dried over anhydrous Na2SO4 and concentrated. The crude product was purified by flash chromatography, affording the title compound (off white solid). 1H NMR (400 MHz, DMSO-d6): delta 8.83 (s, 2H), 6.90 (s, 1H), 6.84 (d, J = 7.6 Hz, 1H), 6.74 (dd, J = 8.0, 1.2 Hz, 1H), 5.99-5.98 (m, 2H), 3.84 (t, J = 4.8 Hz, 4H), 3.40-3.36 (m, 1H), 2.49-2.47 (m, 5H), 2.38-2.35 (m, 2H), 1.27 (d, J = 6.8 Hz, 3H). LCMS: (Method A) 355.0 (M+H), Rt. 2.61 min, 99.78% (Max). HPLC: (Method A) Rt. 2.55 min, 99.51 % (Max).

With the rapid development of chemical substances, we look forward to future research findings about 110100-00-0.

Reference:
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (243 pag.)WO2016/30443; (2016); A1;,
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Electric Literature of 862730-04-9, Adding some certain compound to certain chemical reactions, such as: 862730-04-9, name is 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine,molecular formula is C8H10IN5, 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 862730-04-9.

Synthesis of (3-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)methanol (BA26); A solution of (3-Hydroxymethylphenyl)boronic acid (24 mg, 0.13 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (20 mg, 0.07 mmol) in DME (12 ml). Pd(PPh3)4 (16 mg, 0.014 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA26 (8.4 mg, 42% yield). ESI-MS (M+H)+ m/z calcd 283.1, found 284.2.

According to the analysis of related databases, 862730-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); 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.1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, molecular weight is 146.53, as common compound, the synthetic route is as follows.category: pyrimidines

General procedure: A mixture of 5-fluorouracil (50.5 mg, 0.39 mmol), pyridine (0.60 mL), and HMDS (1.2 mL) in a20-mL Schlenk tube was refluxed (oil bath temp., 140 C) for ca. 30 min to give a clear solution of 2a. All the volatiles were then removed under reduced pressure (ca. 1mmHg) to give a clear syrup, which was dissolved in MeCN (3.0 mL). To this were added 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (1) (151.5 mg, 0.30 mmol) and6 (5.8 mg, 15 mumol), and the mixture was stirred under reflux (oil bath temp., 80 C) for6 h. The reaction mass was cooled to rt and EtOAc (2 mL) was added to it, followed by saturated NaHCO3 solution (2 mL). After the mixture was stirred at 0 C for 15min, EtOAc (30 mL) and saturated NaHCO3 solution (20 mL) were added to it. The organic phase was separated and the aqueous phase was back-extracted with EtOAc (3 x30 mL). The combined organic layer was dried over Na2SO4 and evaporated to afforda foamy white crude material, which was crystallized from EtOAc (10 mL) and hexane(20 mL) as a white solid (139.2 mg). The mother liquor was purified by column chromatography (Silica Gel 60, 8 g, EtOAc:hexane = 30:70 35:65) to afford the titlecompound 3a (15.6 mg). The combined yield was 90% (155 mg). 1H and 13C NMR spectra were consistent with the reported ones.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1820-81-1, 5-Chlorouracil, and friends who are interested can also refer to it.

Reference:
Article; Basu, Nabamita; Oyama, Kin-ichi; Tsukamoto, Masaki; Tetrahedron Letters; vol. 58; 20; (2017); p. 1921 – 1924;,
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Pyrimidine – Wikipedia

Application of 42839-09-8, 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 42839-09-8, name is 2-Pyrimidinemethanol. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 9 A mixture of 7.2 g. of 2-pyrimidinemethanol and 25 ml. of thionyl chloride is heated for 4 hours on a steam bath, then concentrated under reduced pressure. The residue is dissolved in water and basified with 5% aqueous sodium bicarbonate solution. Extracting with ether, then drying and concentrating the extracts gives 2-(chloromethyl)pyrimidine.

According to the analysis of related databases, 42839-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Corporation; US3966945; (1976); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 696-07-1, Adding some certain compound to certain chemical reactions, such as: 696-07-1, name is 5-Iodouracil,molecular formula is C4H3IN2O2, 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 696-07-1.

General procedure: To a solution of 5-iodopyrimidine (0.84 mmol) in anhydrous DMF (7 mL) were added the terminal alkyne (2.5 mmol), Pd(PPh3)4 (0.08 mmol), CuI (0.08 mmol) and Et3N [or (iPr)2EtN] (1.68 mmol). Method A: The reaction mixture was stirred at room temperature overnight. The extent of the reaction was monitored by TLC and the solvent was evaporated in vacuo and the residue purified by column chromatography (initial eluent CH2Cl2, then CH2Cl2/MeOH = 40:1) to afford 1-10a and 1-6b. Method B: The synthesis was carried out at 50 C for 30 min under microwave irradiation (300 W, 1 bar, Milestone start S microwave oven). Purification by column chromatography (initial eluent CH2Cl2, then CH2Cl2/MeOH = 40:1) afforded compounds 1-10a and 1-6b.

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. 696-07-1, 5-Iodouracil, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kraljevi?, Tatjana Gazivoda; Bistrovi?, Andrea; Dedi?, Matea; Paveli?, Sandra Kraljevi?; Sedi?, Mirela; Rai?-Mali?, Silvana; Tetrahedron Letters; vol. 53; 38; (2012); p. 5144 – 5147;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 40805-79-6, 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 40805-79-6, name is 5-Pyrimidinecarbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

In a 250 mL round-bottomed flask, pyrimidine-5-carbonitrile (1.5 g, 14.3 mmol), pyridine (0.339 g, 0.35 ml, 28.5 mmol), and 2-mercaptopropionic acid (1.51 g, 14.3 mmol) were combined to give a light yellow solution. The reaction mixture was heated to 100 C. and stirred for 2 h. Upon cooling, the thick yellow mixture was diluted with 100 mL ethanol and stirred for 30 min. The slurry was then filtered, and washed with diethyl ether (2*100 mL) to give 5-Methyl-2-(pyrimidin-2-yl)-thiazol-4-ol (2.33 g, 85%) as yellow solid which was used directly without further purification.

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 40805-79-6, 5-Pyrimidinecarbonitrile.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 10397-13-4, 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. 10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine. A new synthetic method of this compound is introduced below.

4-(4,6-dichloropyrimidin-2-yl)morpholine (lOOmg 0.43mmol), pyridine-3-boronic acid (49mg, 0.4mmol), Cs2C03 ( 280mg, 0.86mmol) and Pd(PPh3)2Cl2 (20mg, 0.025mmol) were combined in dioxane (3ml) and water (1ml). The reaction mixture was then heated by microwave at 120C for 20min. Without purification (4-(3-cyclopropylureido)phenyl)boronic acid pinacol ester (130mg, 0.43mmol), Cs2C03 ( 280mg, 0.86mmol) and Pd(PPh3)2Cl2 (20mg, 0.025mmol) were added and the reaction mixture was then heated by microwave at 120C for a further 20min. The reaction mixture was partitioned between EtOAc and water. The organic layer was passed through a PTFE hydrophobic frit and the solvent removed in vacuo. Residual solid was triturated to give crude produect which was further purifed by prep LC/MS (low pH) to yield (9mg, 5%). 1H NMR (dg-DMSO) 9.45 (s, 1H), 8.72 (d, 1H), 8.65 (s, 1H), 8.61 (d, 1H), 8.22 (d, 2H), 7.87 (s, 1H), 7.58-7.55 (m, 3H), 6.51 (br s, 1H), 3.93-3.86 (m, 4H) 3.76-3.71 (m, 4H), 2.58-2.52 (m, 1H), 0.67-0.62 (m, 2H), 0.44-0.40 (m, 2H);LCMS (method B), (M+H+) 417, Rt = 2.24min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10397-13-4, 4-(4,6-Dichloropyrimidin-2-yl)morpholine, and friends who are interested can also refer to it.

Reference:
Patent; CELLZOME LIMITED; LYNCH, Rosemary; CANSFIELD, Andrew, David; NIBLOCK, Helen, Sarah; HARDY, Daniel, Paul; TAYLOR, Jessica; WO2011/107585; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia