Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 41103-17-7, Ethyl 4-chloropyrimidine-5-carboxylate, 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: C7H7ClN2O2, blongs to pyrimidines compound. HPLC of Formula: C7H7ClN2O2

To a stirred solution of ethyl 4-chloropyrimidine-5-carboxylate (1 g, 5.35 mmol) in toluene (50 mL) under an inert atmosphere was added cyclopropylboronic acid (829 mg, 9.64 mmol) and cesium carbonate (2.62 mg, 8.03 mmol) at room temperature in a sealed tube. The reaction mixture was degassed under argon for 15 min. Pd(dppf)Cl2 (218 mg, 0.26 mmol) was added at room temperature and the solution was degassed under argon for another 10 min. The reaction mixture was heated to 100 C. and stirred for 5 h. After consumption of starting material (by TLC), the reaction mixture was filtered through a pad of celite, and the pad was washed with EtOAc (100 mL). The filtrate was concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluent: 20% EtOAc/Hexane) to afford ethyl 4-cyclopropylpyrimidine-5-carboxylate (150 mg, 0.78 mmol, 15%) as a pale yellow syrup. 1H NMR (400 MHz, DMSO-d6): delta 9.08 (s, 1H), 8.98 (s, 1H), 4.37 (q, J=7.1 Hz, 2H), 3.01-2.93 (m, 1H), 1.35 (t, J=7.1 Hz, 3H), 1.18-1.15 (m, 4H) LC-MS: m/z 192.9 [M+H]+ at 2.40 RT (95.93% purity)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,41103-17-7, Ethyl 4-chloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; (93 pag.)US2018/186773; (2018); A1;,
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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 16234-10-9, name is Thieno[3,2-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 16234-10-9

4-Chlorothieno[3, 2-d]pyrimidine VlTo a solution of 6.12 ml of dimethylformannide in 45 ml of methylene chloride is added dropwise at 25C a solution of 9.95 ml of oxalyl chloride in 45 ml of methylene chloride. Subsequently, 5.5 g of compound Vila are added and then the mixture is heated at reflux for 2.5 hours. The reaction mixture is added cautiously to water and extracted three times with methylene chloride. The combined organic phases are dried over sodium sulphate and, after filtration, concentrated under reduced pressure. After drying under reduced pressure, 4.9 g of compound Vl are obtained as a crude product, which is reacted further without further purification.NMR (300 MHz, DMSO-d6): delta = 7.73 (1 H), 8.57 (1 H), 9.01 (1 H).

With the rapid development of chemical substances, we look forward to future research findings about 16234-10-9.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2009/7421; (2009); A1;,
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Reference of 4359-87-9, 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. 4359-87-9, name is 2,4,6-Trichloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Preparation of 2,6-dichloro-5-nitro-4-morpholino-pyrimidine. To a solution of 2,4,6-trichloronitropyrimidine (6.20 g, 27.2 mmol) in CH2Cl2 (170 mL) at 0 C. was added a solution of morpholine (2.34 g, 27.2 mmol) and NEt3 (2.74 g, 27.2 mmol) in CH2Cl2 (70 mL) over a period of 1 hr. The reaction mixture was stirred for another 1 hr at 0 C. and allowed to warm to 20 C. and stirred for 12 hours to drive the reaction to competition. For purification, silica gel (20 g) was added to the reaction mixture and the solvent was removed so that product was adsorbed on the silica gel. The material was purified by flash chromatography using CH2Cl2 eluent the product was obtained as yellow solid after concentration. Yield: 6.90 g, 91%. MS (ESI) m/z 279.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4359-87-9, its application will become more common.

Reference:
Patent; Wyeth; US2009/181963; (2009); A1;,
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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. 14048-15-8, name is 2,4-Dimethoxypyrimidin-5-amine, molecular formula is C6H9N3O2, 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. Application In Synthesis of 2,4-Dimethoxypyrimidin-5-amine

In a 250 mL round-bottomed flask equipped with magnetic stirring bar, compounds C-4A (11.6 g, 47 mmol, 1 eq), C-7A (8.7 g, 56 mmol, 1.2 eq) and C-6F (10 g, 47 mmol, 1 eq) were suspended in 75 mL of AcOH, and the flask was tightly closed with plastic stopper. The mixture was heated up to 70 C and stirred at this temperature for 24 h. After that time UPLCMS analysis showed 47 % of the expected product. The reaction mixture was evaporated to dryness. The solid residue was preadsorbed onto silicagel and purified using flash chromatography (20 % to 50 % of AcOEt in n-hexane). All fractions which contained the product were evaporated to dryness to furnish 6.6 g of the desired product C-8.C10, with 83 % purity according to UPLCMS analysis. Yield: 32 %.

With the rapid development of chemical substances, we look forward to future research findings about 14048-15-8.

Reference:
Patent; Adamed sp. z o.o.; FEDER, Marcin; MAZUR, Maria; KALINOWSKA, Iwona; JASZCZEWSKA, Joanna; LEWANDOWSKI, Wojciech; WITKOWSKI, Jakub; JELEN, Sabina; WOS-LATOSI, Katarzyna; (56 pag.)EP3511334; (2019); A1;,
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Related Products of 799842-07-2 , The common heterocyclic compound, 799842-07-2, name is N-[5-Bromomethyl-4-(4-fluorophenyl)-6-isopropylpyrimidine-2-yl]-N-methylmethane sulfonamide, molecular formula is C16H19BrFN3O2S, 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.

General procedure: Aq 1 M NaOH (9 mL, 1.5 equiv) was added to a stirred MeOH (20mL) solution of the appropriate aromatic thiol (7.2 mmol, 1.2equiv). The solution was stirred at r.t. for 15 min and then the heterocyclicalkyl bromide 2 or 3 (6 mmol, 1 equiv) was added. When rosuvastatin moiety bromides 2 were used, THF (10 mL) was also added to the mixture to improve solubility. After 18 h, the solvent was evaporated, the residue was dissolved in CH2Cl2 (50 mL), and washed with H2O (100 mL). The aqueous phase was additionally extracted with CH2Cl2 (2 × 25 mL). The combined organic phases were dried (MgSO4) and the solvent was evaporated. The residuewas recrystallized and the isolated product was dried in vacuumovernight at 60 C below 50 mbar to give the pure sulfide heterocyclic precursor 4 or 5 in 75-97% yield.

The synthetic route of 799842-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fabris, Jan; ?asar, Zdenko; Smilovi?, Ivana Gazi?; ?rnugelj, Martin; Synthesis; vol. 46; 17; (2014); p. 2333 – 2346;,
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Related Products of 153435-63-3, 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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

Intermediate 50: 3-Fluoro-2-(pyrimidin-2-yl)benzoic acid.Step A: 3-Fluoro-2-(pyrimidin-2-yl)benzonitrile. 2-lodo-3- fluorobenzonitrile (2.5 g, 10.3 mmol) and 2-tributylstannane pyrimidine (3.7g, 10.0 mmol) were combined and dissolved in degassed DME (18 ml) then purged with bubbling N2 for 5 minutes. The reaction was treated withPd(PPh3)4 (577 mg, 0.5 mmol) and then purged with bubbling for 5 minutes in a sealed vessel and then heated in microwave at 160 C for 90 min. The reaction was cooled and filtered through celite and concentrated to minimum volume and the ppt the formed was diluted with hexanes (40 ml) and cooled to 0 C then filtered. The solid purified (FCC) (20-100% EA / hex) to give 3-fluoro- 2-(pyrimidin-2-yl)benzonitrile. 1 H NMR (400 MHz, CDCI3): 8.93 (d, J = 4.9 Hz, 2H), 8.14 (dd, J = 9.6, 2.7 Hz, 1 H), 7.86 (dd, J = 8.6, 5.3 Hz, 1 H), 7.36 (t, J = 4.9 Hz, 1 H), 7.32 – 7.24 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
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Electric Literature of 13036-57-2, 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. 13036-57-2, name is 2-Chloro-4-methylpyrimidine. A new synthetic method of this compound is introduced below.

A 1.3 M lithium hexadisilazide-THF solution (179 mL) was added dropwise to a mixture containing methyl nicotinate (16.0 g), 2-chloro-4-methylpyrimidine (15.0 g)and THF (179 mL) under a nitrogen atmosphere while maintaining the internal temperature at about -30 C., and the mixture was stirred at -30 C. for 30 minutes, and then at room temperature for 1 hour. A saturated ammonium chloride aqueous solution was added to the reaction mixture, and extraction was performed using ethyl acetate. Then, an organic layer was dried with anhydrous sodium sulfate and concentrated under a reduced pressure. The obtained residue was purified through silica gel column chromatography (elution solvent: ethyl acetate), and then solidified in methyl tert-butyl ether, and thereby 2-(2-chloropyrimidin-4-yl)-1-(pyridin-3-yl)ethan-1-one (19.2 g)as an orange solid was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13036-57-2, 2-Chloro-4-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; RIKEN; THE UNIVERSITY OF TOKYO; HASHIZUME, Yoshinobu; SEKIMATA, Katsuhiko; KUBOTA, Hirokazu; YAMAMOTO, Hirofumi; KODA, Yasuko; KOYAMA, Hiroo; TAGURI, Tomonori; SATO, Tomohiro; TANAKA, Akiko; MIYAZONO, Kohei; (156 pag.)US2019/337926; (2019); A1;,
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;,
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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. 1152107-25-9, name is Gsk-1322322. A new synthetic method of this compound is introduced below., Recommanded Product: Gsk-1322322

Example 8 [(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-6-[(9aS)-hexahydropyrazino [2,1 -c] [1 ,4] oxazin- 8(1 H)-yl]-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl] hydroxyl formamide dimethanesulphonate. Crystalline [(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-6-[(9aS)- hexahydropyrazino[2, 1 -c][1 ,4]oxazin-8(1 H)-yl]-2-methyl-4-pyrimidinyl}hydrazino)-3- oxopropyl]hydroxyformamide (100 mg) was dissolved in ethyl acetate (10 ml_). Methanesulphonic acid (40.1 mg) in ethyl acetate (ca. 10 ml.) was prepared. The methanesulphonic acid solution was added dropwise to the solution of freebase in ethyl acetate. A precipitate was formed. The slurry was stirred and aged overnight. The precipitate’s crystallinity was verified by polarized light microscopy. The precipitate and supernatant were separated by filtration. The solids were then vacuum dried. The resulting solid was analytically characterized and found to be Form 1 of the dimethanesulphonate salt of [(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-6-[(9aS)- hexahydropyrazino[2, 1 -c][1 ,4]oxazin-8(1 H)-yl]-2-methyl-4-pyrimidinyl}hydrazino)-3- oxopropyl]hydroxyformamide by XRPD (see Figure 7). X-Rav Powder Diffraction of r(2R)-2-(Cvclopentylmethyl)-3-(2-f5-fluoro-6-r(9aS)- hexahvdropyrazinor2,1-ciri,41oxazin-8(1 H)-vn-2-methyl-4-pyrimidinyl>hvdrazino)-3- oxopropyUhydroxyformamide dimethanesulphonate The XRPD pattern for polymorphic Form 1 of [(2R)-2-(Cyclopentylmethyl)-3-(2-{5- fluoro-6-[(9aS)-hexahydropyrazino[2, 1 -c][1 ,4]oxazin-8(1 H)-yl]-2-methyl-4- pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide dimethanesulphonate is presented in Figure 7. The X-ray powder diffractogram was collected with a diffraction system utilizing copper Ka radiation, automated divergent slits, nickel Kappabeta filter, and multiple strip detector. Sample presentation consisted of a thin powder layer mounted on a silicon zero background wafer. Thermal Analysis Based on differential scanning calorimetry (DSC) seen in Figure 8 and thermogravimetric analysis (TGA) seen in Figure 9, polymorphic Form 1 of [(2R)-2- (cyclopentylmethyl)-3-(2-{5-fluoro-6-[(9aS)-hexahydropyrazino[2,1 -c][1 ,4]oxazin-8(1 h)-yl]- 2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide dimethanesulphonate decomposes at ca. 180 to 185 C under nitrogen.

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, 1152107-25-9, Gsk-1322322.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO. 2) LIMITED; AUBART, Kelly, Marshall; GILLIAN, Jason, Michael; QIN, Donghui; MCKEOWN, Robert, Rahn; WILLIAMS, Glenn, R.; WO2013/82388; (2013); A1;,
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Synthetic Route of 1195768-23-0, 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. 1195768-23-0, name is N-(3-(2-(tert-Butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide. A new synthetic method of this compound is introduced below.

Step D : N- { 3 – [ 5-(2-amino-4-pyrimidiny l)-2-( 1 , 1 -dimethy lethyl)- 1 ,3 -thiazol-4-yl] -2- fluorophenyl} -2,6-difluorobenzenesulfonamide: In 1 gal pressure reactor, a mixture of N- {3-[5-(2-chloro-4-pyrimidinyl)-2-(l,l- dimethylethyl)-l,3-thiazol-4-yl]-2-fluorophenyl} -2,6-difluorobenzenesulfonamide (120 g) prepared in accordance with Step C, above, and ammonium hydroxide (28-30%, 2.4 L, 20 vol) was heated in the sealed pressure reactor to 98-103 C and stirred at this temperature for 2 hours. The reaction was cooled slowly to room temperature (20 C) and stirred overnight. The solids were filtered and washed with minimum amount of the mother liquor and dried under vacuum. The solids were added to a mixture of EtOAc (15 vol)/ water (2 vol) and heated to complete dissolution at 60-70 C and the aqueous layer was removed and discarded. The EtOAC layer was charged with water (1 vol) and neutralized with aq. HC1 to ~pH 5.4-5.5. and added water (lvol). The aqueous layer was removed and discarded at 60-70 C. The organic layer was washed with water (1 vol) at 60-70 C and the aqueous layer was removed and discarded. The organic layer was filtered at 60 C and concentrated to 3 volumes. EtOAc (6 vol) was charged into the mixture and heated and stirred at 72 C for 10 min , then cooled to 20C and stirred overnight. EtOAc was removed via vacuum distillation to concentrate the reaction mixture to ~3 volumes. The reaction mixture was maintained at ~65-70C for ~30mins. Product crystals having the same crystal form as those prepared in Example 58b (and preparable by the procedure of Example 58b), above, in heptanes slurry were charged. Heptane (9 vol) was slowly added at 65-70 C. The slurry was stirred at 65-70 C for 2-3 hours and then cooled slowly to 0-5C. The product was filtered, washed with EtO Ac/heptane (3/1 v/v, 4 vol) and dried at 45 C under vacuum to obtain N- {3 – [5 -(2-amino-4-pyrimidinyl)-2-( 1 , 1 -dimethylethyl)- 1 , 3 -thiazol-4-yl] -2- fluorophenyl}-2,6-difluorobenzenesulfonamide (102.3 g, 88%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1195768-23-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; CAPONIGRO, Giordano; HORN-SPIROHN, Thomas; LEHAR, Joseph; (49 pag.)WO2017/37587; (2017); A1;,
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