Pyrimidines

Application of 35265-83-9, Adding some certain compound to certain chemical reactions, such as: 35265-83-9, name is 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine,molecular formula is C7H4Cl2N2S, 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 35265-83-9.

Reference Example 35 2-Chloro-7-methyl-4-piperidinoaminothieno[3,2-d] pyrimidine In DMF (N,N-dimethylformamide) was dissolved 700 mg (3.4 mmol) of 2,4-dichloro-7-methylthieno[3,2-d] pyrimidine, and then a solution of 751 mg (7.5 mmol) of 1-aminopiperidine was added dropwise to the resulting solution under ice cooling over 5 minutes. The reaction solution was stirred at 0C. for one hour and then allowed to resume room temperature, followed by stirring for further one hour. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml*3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane= 1/8) to give 573 mg (yield: 59.4%) of the title compound. NMR (delta, CDCl3): 1.20-1.28 (1H, m), 1.76-1.91 (5H, m), 2.41 (3H, s), 2.44-2.49 (2H, m), 3.17-3.20 (2H, m), 6.46 (1H, s), 7.46 (1H, s)

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. 35265-83-9, 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NAKASHIMA, YOSHIHARU; FUJITA, TAKASHI; HIZUKA, MICHIYO; IKAWA, HIROSHI; HIRUMA, TORU; US2001/6969; (2001); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 461-98-3, 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. 461-98-3, name is 2,6-Dimethylpyrimidin-4-amine. A new synthetic method of this compound is introduced below.

2-(2,6-Dimethyl-pyrimidin-4-ylamino)-thiazole-5-carbonitrile (22-3) 4-amino-2,6-dimethylpyrimidine (93 mg, 0.76 mmol)was dissolved in 1.4 mL anhydrous DMF and sodium hydride (66mg, 60% dispersion, 2.77 mmol) was added at room temperature. When the bubbling stopped, 2-chloro-thiazole-5-carbonitrile (0.100 g, 0.692 mmol) was added and the reaction was stirred at room temperature. After 4 hours, 1M HCl was added until the solution was neutral. The resulting precipitate was filtered, washed with water, and dried under high vacuum. The material was washed with hexane and filtered again and air dried to afford the title compound. 1H-NMR (300 MHz, DMSO-d6) 12.47 (1H,s), 8.32 (1H,s), 6.75 (1H,s), 2.58 (3H,s), 2.38 (3H,s). M+1=232.1. MP>250

At the same time, in my other blogs, there are other synthetic methods of this type of compound,461-98-3, 2,6-Dimethylpyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Bilodeau, Mark T.; Hartman, George D.; Hoffman JR., Jacob M.; Sisko, John T.; Manley, Peter J.; Smith, Anthony M.; Tucker, Thomas J.; Lumma JR., William C.; Rodman, Leonard; US2002/137755; (2002); A1;,
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Related Products of 98136-42-6, 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. 98136-42-6, name is 2,6-Dichloropyrimidine-4-carboxamide. A new synthetic method of this compound is introduced below.

To a mixture of 2,6-dichloropyrimidine-4-carboxamide (4.800 g, 25.00 mmol) in acetonitrile (100 mL) was added (S)-methyl 2-aminopropanoate hydrochloride (3.565 g, 25.54 mmol) and iPr2NEt (9.60 mL, 55.1 1 mmol). The mixture was heated at 50C overnight then concentrated in vacuo. The residue was chromatographed over silica gel with 20-60% acetone in hexanes. Two isomers were obtained from the chromatography. The first isomer to elute was (S)-methyl 2-((6-carbamoyl-2- chloropyrimidin-4-yl)amino)propanoate (A) and the second to elute was (S)-methyl 2-((4-carbamoyl-6-chloropyrimidin-2-yl)amino)propanoate (B). Separately, the appropriate product fractions were evaporated in vacuo to give (S)-methyl 2-((6- carbamoyl-2-chloropyrimidin-4-yl)amino)propanoate (A) as a pale tan powder (5.133 g, 19.84 mmol, 79% yield). LC/MS: m/z= 259.2 [M+H]+ and (S)-methyl 2-((4- carbamoyl-6-chloropyrimidin-2-yl)amino)propanoate (B) as a tan powder (0.652 g, 2.52 mmol, 10% yield). LC/MS: m/z= 259.2 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98136-42-6, 2,6-Dichloropyrimidine-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; PURDUE PHARMA L.P.; LOCKMAN, Jeffrey; NI, Chiyou; PARK, Jae Hyun; PARK, Minnie; SHAO, Bin; TAFESSE, Laykea; YAO, Jiangchao; YOUNGMAN, Mark, A.; WO2014/135955; (2014); A1;,
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Application of 54660-78-5 ,Some common heterocyclic compound, 54660-78-5, molecular formula is C4H4ClN3, 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.

0058] At room temperature, NaH (67 mg, 2.79 mmol) was added to a solution of tert-butyl 4-(hydroxymethyl) piperidine-1-carboxylate (131) (500 mg, 2.32 mmol) in THF (tetrahydrofuran) (10 mL) and stirred for 1 hour. 4-chloro-pyrimidin-5-amine (A) (346 mg, 2.67 mmol) was then added. The reaction mixture was then heated to 100¡ãC under nitrogen and stirred for 4 hours, cooled to room temperature (20-30¡ãC) and concentrated in vacuo. The residue was purified with flash column (eluent: 10-30percentethyl acetate/petroleum ether) to obtain the product C1 (308mg, 1.0 mmol).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54660-78-5, its application will become more common.

Reference:
Patent; NuBridge BioSciences; ZHANG, Lin; (30 pag.)US2017/101395; (2017); A1;,
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Related Products of 56181-39-6, 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.56181-39-6, name is 5-Bromo-4-chloropyrimidine, molecular formula is C4H2BrClN2, molecular weight is 193.4291, as common compound, the synthetic route is as follows.

Step 4. tert-butyl 6-(5-bromopyrimidin-4-yl)-2,6-diazaspiro[3.3]heptane-2-carboxylate (0755) A suspension of 5-bromo-4-chloropyrimidine (1.67 g, 8.65 mmol), tert-butyl 2,6- diazaspiro[3.3]heptane-2-carboxylate hemioxalate salt (2 g, 4.12 mmol) and iPr2NEt (1.80 mL, 10.3 mmol) in iPrOH (10 mL) was heated at reflux for 15 h. Saturated NH4Cl aqueous solution (10 mL) and EtOAc (20 mL) were added to the reaction for the workup. The EtOAc layer was separated and the aqueous layer was extracted again with EtOAc. The EtOAc layers were combined, washed with water, then brine, and dried using Na2SO4. Evaporation of the EtOAc gave tert-butyl 6-(5-bromopyrimidin-4-yl)-2,6- diazaspiro[3.3]heptane-2-carboxylate as an off-white foamy solid (2 grams, 70%) that was nearly pure by LCMS analysis and used directly for the next step without further purification. LCMS method A: tR = 1.330 min; [M + H]+ = 355.41 and 357.

The chemical industry reduces the impact on the environment during synthesis 56181-39-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 289042-12-2, tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate, 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, Safety of tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate, blongs to pyrimidines compound. Safety of tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

10 g of tert-butyl 2-((4R,6S)-6-((E)-2-(4-(4′-fluorophenyl)-6-isoIrIpyl-2- (methylamino)pyrimidin-5-yl)vinyl)-2,2-dimethyl- 1 ,3 -dioxan-4-yl)acetate of formula (4) and 100 mL of methylene dichloride was taken into 500 mL RBF. 25 g of triethylamine was added into the reaction mixture at 250C to 35AC. The reaction mixture was cooled to get -2O0C to -250C and treated with methane sulphonyl chloride. After maintaining for 1 hour under stirring, upon completion of reaction on TLC, the reaction mixture is quenched into 100 gm ice at 00C to 50C. Separated organic layer was washed with water and 80% methylene dichloride was distilled atmospherically at 4O0C to 500C. The reaction mixture was treated with 21 mL 10% sodium hydroxide solution and 100 mL methanol. The remaining methylene dichloride was removed azeI?lropically at 450C to 5O0C. After MDC removal, the reaction mixture was treated with 200 mL methanol and temperature was raised upto reflux for about 60AC to 650C for 6-8 hours. After the completion of the reaction on TLC, methanol was distilled under vacuum at 4O0C to 45AC.Further, the reaction mixture was treated with 20 mL of water and 50 mL of acetonitrile and cooled to O0C to 1O0C. The pH of the reaction mixture was adjusted using dil HCl at O0C to 1O0C. The organic layer was separated and treated with n-propyl amine to adjust the pH to about 8 to 9 at O0C to 1O0C. The reaction mixture was maintained at about 25AC to 350C for 1 hour. The product thus obtained was filtered and washed with chilled with acetonitrile. The solid was dried at 5O0C to 550C to obtain n-propyl amine salt of 2-((4R,6S)-6-((E)-2-(4-(4′-fluoroIhenyl)-6-isoIroIyl-2-(N- mI-thylmethylsulfonamido)pyriniidin-5-yl)vinyl)-2,2-dimethyl-l,3-dioxan-4-yl) acetic acid of formula (2′).

The synthetic route of 289042-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CADILA HEALTHCARE LIMITED; WO2009/157014; (2009); A2;,
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Adding a certain compound to certain chemical reactions, such as: 7752-82-1, 5-Bromopyrimidin-2-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, Computed Properties of C4H4BrN3, blongs to pyrimidines compound. Computed Properties of C4H4BrN3

Method 1 [0079] S idine-2-ylamine[0080] To a dry 500-mL flask was added 2-amino-5-bromopyrimidine (10 g, 57.5 mmol), potassium acetate (16.9 g, 172 mmol), 4,4,5, 5-tetramethyl-2-(4,4,5,5-tetramethyl-l, 3,2- dioxaborolan-2yl)-l ,3,2-dioxaborolane (16.1 g, 63.0 mmol) and dioxane (300 mL). Argon was bubbled through the solution for 15 minutes, at which time dichloro[l,l’- bis(diphenylphosphino)ferrocene] palladium (II) dichloromethane adduct (Pd(dppf)Cl2 CH2CI2) (2.34 g, 2.87 mmol) was added. The reaction mixture was refluxed in a 115 C oil bath for 4 hours under argon. After cooling to room temperature, EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were washed with H20 (2×300 mL), NaCl(Sat.) (300 mL), dried over Na2S04, and filtered through a 5 cm pad of silica gel.Additional EtOAc was used to flush product. After the solvent was concentrated, the crude was treated with a mixture of 1 :3 dichloromethane and hexane (40 mL), filtered and washed with hexane yielding a light yellow solid (8.5 g, 75%). LCMS (m/z): 140 (MH+ of boronic acid, deriving from product hydrolysis on LC). ? NMR (CDC13): delta 8.58 (s, 2H), 5.74 (s, 2H), 1.32 (s, 12H).

The synthetic route of 7752-82-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 33034-67-2, 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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Preparative Example 3 N-(3-Bromophenyl)-4-(trifluoromethyl)pyrimidin-2-amine A solution of 3-bromoaniline (250 g, 1.46 mol) in dioxane (2.5 L) was prepared, and 2-chloro-4-(trifluoromethyl)pyrimidine (267 g, 1.47 mol) and methanesulfonic acid (155 g, 1.61 mol) were added sequentially. The resulting solution was heated to 100 ¡ãC overnight. The resulting mixture was cooled and concentrated under reduced pressure. The residue was adjusted to pH 7-8 with aqueous sodium bicarbonate solution. The solid was filtered, and the filtrate was extracted with EtOAc (4×500 mL) The organic layers were combined, washed with water (2 x 2 L), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford N-(3-bromophenyl)-4-(trifluoromethyl)pyrimidin-2-amine as a light yellow solid. MS APCI [M + 3]+ m/z 319. NMR (500 MHz, CDCI3) delta 8.68 (d, / = 4.9 Hz, 1 H), 7.95 (s, 1 H), .53-7.50 (m, 1 H), 7.44 (br s, 1 H), 7.22 (m, 2 H), 7.08 (d, / = 4.9 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33034-67-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michelle R.; ROMEO, Eric T.; KATTAR, Solomon D.; CHRISTOPHER, Matthew; ALTMAN, Michael D.; NORTHRUP, Alan B.; ELLIS, John Michael; BOYLE, Brendan O’; DONOFRIO, Anthony; GRIMM, Jonathan; REUTERSHAN, Michael H.; CHILDERS, Kaleen Konrad; OTTE, Ryan D.; CASH, Brandon; DUCHARME, Yves; HAIDLE, Andrew M.; SPENCER, Kerrie; VITHARANA, Dilrukshi; WU, Lingyun; ZHANG, Li; ZHANG, Peng; BEAULIEU, Christian; GUAY, Daniel; WO2014/48065; (2014); A1;,
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Reference of 1546-78-7, Adding some certain compound to certain chemical reactions, such as: 1546-78-7, name is 4-Hydroxy-6-(trifluoromethyl)pyrimidine,molecular formula is C5H3F3N2O, 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 1546-78-7.

Add 6-(trifluoromethyl)pyrimidin-4-ol (1.5 g, 9.15 mmol) and oxalyl chloride (2.3 mL, 22.9 mmol) to EtOAc (15 mL), then add 5 drops of DMF. Heat the mixture to reflux for 2 hrs. After reaction, partition between EtOAc and brine, separate the organic layer; dry the organic layer over anhydrous Na2S04. Transfer the organic solution to a sealed tube, add a solution of NH3 in methanol (7M, lOmL), seal the tube, heat at 70C for 15 hrs. Cool to room temperature; concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, EtOAc_PE=2:l) affords the target compound (920 mg, 61.3%).

According to the analysis of related databases, 1546-78-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHANG, Deyi; ZHANG, Ruihao; ZHONG, Boyu; SHIH, Chuan; WO2014/418; (2014); A1;,
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. 4595-61-3, name is Pyrimidine-5-carboxylic acid, molecular formula is C5H4N2O2, 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. HPLC of Formula: C5H4N2O2

5-Pyrimidinecarboxylic acid (500mg) in thionyl chloride (5mL) was stirred at 110¡ãC5 under nitrogen for 1h. The solvent was evaporated under vacuum to give 5-pyrimidinecarbonyl chloride as a brown oil (505mg). (4-Bromo-2-fluorophenyl)(iodo)zinc intetrahydrofuran (0.5M, 7.0ml_) was added slowly to a stirred mixture of the acid chloride(500mg) and tetrakis(triphenylphosphine)palladium(0) (203mg) in tetrahydrofuran (3mL) atroom temperature under nitrogen then stirred at room temperature for 1h. Aqueous10 ammonium chloride (1M, 5mL) was added and the mixture was absorbed onto silica andpurified by chromatography on a silica column eluting with a cyclohexane/ethyl acetategradient to give the title compound (712mg).LC-MS: Rt 2.65min.

With the rapid development of chemical substances, we look forward to future research findings about 4595-61-3.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/73189; (2005); A1;,
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Pyrimidine – Wikipedia