Category: pyrimidines

Adding a certain compound to certain chemical reactions, such as: 99420-75-4, 5-Methylpyrimidine-2-carboxylic 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

To a solution of 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF(72.4 mL) was added 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24mmol), and N,Odimethylhydroxylaminehydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to0 C and 1-propanephosphonic acid cyclic anhydride, 50 wt.% solution in EtOAc (9.21mL, 14.48 mmol) was added dropwise. The mixture was allowed to warm toRTovernight. LCMS indicated complete conversion to product. The mixture was dilutedwith water, extracted with CHCb:IPA (3:1) and washed with brine and NaHC03. Themixture was then dried over Na2S04, concentrated in vacuo and purified by silica gelchromatography (0-100% heptanes:EtOAc) to yield Example 209.11 (0.7 g, 3.86 mmol,53.4% yield). 1H NMR (500 MHz, CDCb) o 8.61- 8.69 (m, 2 H) 3.61 -3.79 (m, 3 H)3.27- 3.47 (m, 3 H) 2.34- 2.45 (m, 3 H). LCMS-ESI (pos) m/z: 182.2 (M+Ht.

The synthetic route of 99420-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; (434 pag.)WO2018/93577; (2018); A1;,
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Pyrimidine – Wikipedia

Application of 69696-37-3 , The common heterocyclic compound, 69696-37-3, name is 5-Bromo-2,4-dimethylpyrimidine, molecular formula is C6H7BrN2, 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.

Example 60 -((3-carbamoyl-7-(2,4-dimethylpyrimidin-5-yl)-8-fluoroquinolin-4-yl)amino)-5- cyclopentylbenzoic acid a) methyl 3-((3-carbamoyl-7-(2,4-dimethylpyrimidin-5-yl)-8-fluoro 5-cyclopentylbenzoate. A mixture of methyl 3-((7-bromo-3-carbamoyl-8- fluoroquinolin-4-yl)amino)-5-cyclopentylbenzoate (220 mg, 0.452 mmol), bis(pinacolato)diboron (132 mg, 0.520 mmol), potassium acetate (155 mg, 1 .583 mmol), [1 , 1 ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane adduct (18.47 mg, 0.023 mmol) and 1 ,4-dioxane (3 mL) was purged with nitrogen for 15 minutes, then heated at 1 10 C for 30 minutes in a microwave reactor. 5-Bromo-2,4-dimethylpyrimidine (67.7 mg, 0.362 mmol), cesium carbonate (368 mg, 1.131 mmol), [1 , 1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane adduct (18.47 mg, 0.023 mmol) and water (1 mL) were added. The mixture was purged again with nitrogen for 15 minutes, then heated in a microwave reactor at 1 10 C for 30 min. After cooling, the mixture was filtered and then partitioned between ethyl acetate and brine. The combined organics were dried (Na2S04), filtered, and concentrated to a brown residue. This residue was purified on silica gel (0-10% 2- propanol/ethyl acetate, then 10-30% 2-propanol/ethyl acetate) to afford a yellow solid. The solid was further purified by reverse-phase preparative HPLC (ODS, acetonitrile/0.03% aqueous ammonia) to afford the title compound (135 mg, 58%) as a yellow solid. LCMS (ES+) m/e 514 [M+H]+.

The synthetic route of 69696-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROWN, Kristin, K.; CHAI, Deping; DODSON, Christopher, S.; DUFFY, Kevin, J.; SHAW, Antony, Nicholas; WO2013/96151; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 69205-79-4, 2-Amino-4-oxo-4,7-dihydro-3H-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, Formula: C7H5N5O, blongs to pyrimidines compound. Formula: C7H5N5O

In a dry round bottomed flask under an atmosphere of argon, trityl chloride (1.20 g, 4.28 mmol) was added to a solution of 2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (0.50 g, 2.85 mmol) in dry pyridine (29 mL). The mixture reaction was heated at 90 C for 48 h. The reaction mixture was concentrated under reduced pressure then absorbed on silica gel and purified by flash chromatography on silica gel eluting with dichloromethane/MeOH with a gradient starting at 2% of MeOH and rising to lO%. The desired compound wasobtained as a brown solid (0.63 g, 1.5 mmol, 53% yield).Procedure based on Olgen 2008.OH (400 MHz, DMSO-d6) oe 11.80 (br s, 1H); 10.64 (br s, 1H), 7.56 (s, 1H), 7.41(s, 1H), 7.29-7.28 (m, 12H), 7.23-7.17 (m, 3H), 5.73 (s, 1H).HRMS (m/z ESI): C26H18N50 [M-H] Found 416.1514 Requires: 416.1511.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69205-79-4, 2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; KELLY, Vincent; (44 pag.)WO2016/50806; (2016); A1;,
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Application of 60722-67-0, 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. 60722-67-0, name is 2-(Phenylmethoxy)-4-pyrimidinamine. A new synthetic method of this compound is introduced below.

KHMDS, 0.5M solution in toluene (5.95 mL, 2.98 mmol), was added to a stirred solution of the 2-(benzyloxy)pyrimidin-4-amine (0.50 g, 2.48 mmol) in toluene (15 mL) at 0C under nitrogen atmosphere. The reaction was stirred for 30 mm. In another flask, 4- iodobenzoic acid (1,85 g, 7.44 mmol) was dissolved in CH2CI2 (20 mL) under an N2. The solution was cooled to 0 C, oxalyichloride (0.65 mL, 5.16 mmol) was added dropwise followed by the addition of two drops of DMF. The reaction was allowed to stir for 30 mm, until the solution becomes clear. The mixture was concentrated under reduced pressure; the acid chloride formed was dissolved in dichloromethane (10 mL) added into the deprotonated aminopyrimidine dropwise. The reaction was allowed to warm to rt and was stirred overnight. The reaction was quenched with saturated solution of NH4CI (10 mL), extracted with EtOAc (3 x 10 mL). The combined fractions was washed with brine (10 mL) and dried with anhydrous Na2SO4, filtered and concentrated under reduced presure. Purification on silica gel using flash chromatography (10% EtOAc/hexanes) afforded the desired compound as a white solid. MP. 110 C. 1H NMR (500 MHz, CDCI3); ppm 8.50 (d, IH), 8.48 (br s, 1H), 7.96 (d, 1H), 7.88 (d, 2H), 7.60 (d, 2H), 7.47 (d, 2H), 7.38 (t, 2H), 7.34 (t, IH), 5.43 (s, 2H). ?3C NMR (100 MHz, CDCI3); ppm 165.4, 164.7, 160.9, 159.2, 138.5, 136.4, 132.8,128.9, 128.6, 128.2, 128.0, 104.4, 100.6, 69.3. IR(neat); 3303, 3061, 1695, 1585, 1516, 1402, 1288 cm-?. HRMS (ES) Calculated for C,8H,4N3O2Na1 m/z (M+Na) 454.0028, Obs?d.454.0030.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60722-67-0, 2-(Phenylmethoxy)-4-pyrimidinamine, and friends who are interested can also refer to it.

Reference:
Patent; CURZA GLOBAL, LLC; THE UNIVERSITY OF UTAH RESEARCH FOUNDATION; REDDY, Hariprasada R. Kanna; SEBAHAR, Paul R.; SERRANO, Catherine M.; LOOPER, Ryan E.; (117 pag.)WO2019/13789; (2019); A1;,
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Pyrimidine – Wikipedia

Reference of 60025-06-1, Adding some certain compound to certain chemical reactions, such as: 60025-06-1, name is 1-(4,6-Dichloropyrimidin-5-yl)ethanone,molecular formula is C6H4Cl2N2O, 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 60025-06-1.

Step 1 : A solution of 1-(4,6-dichloropyrimidin-5-yl)ethanone (3.81 g, 19.9 mmol) (see Clark et al., J.C.S. Perkin 1 , 1976, 1004) in dioxane (90 mL) was cooled to O0C, and the chilled solution was treated with TEA (2.78 mL, 19.9 mmol) and hydrazine hydrate (1.16 mL, 23.9 mmol). The reaction mixture was then stirred for 18 hr. at 25SC. The mixture was filtered and the precipitate washed with dioxane. The combined filtrates were concentrated, and the resultant residue was chromatographed on silica gel, eluting with 30-35% ethyl acetate/ hexanes to provide 4-chloro-3-methyl-1 H-pyrazolo[3,4-d]pyrimidine (C24). Yield: 2.98 g, 89%. 1H NMR (500 MHz, DMSO-d6) delta: 8.71 (1 H), 2.60 (3H) ppm.

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. 60025-06-1, 1-(4,6-Dichloropyrimidin-5-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/12635; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 19752-61-5, Adding some certain compound to certain chemical reactions, such as: 19752-61-5, name is 5-Bromo-2,4-di-tert-butoxypyrimidine,molecular formula is C12H19BrN2O2, 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 19752-61-5.

iv 5-{5H-Dibenzo[a,d]cyclohepten-5-yl}-2,4(1H,3H)-pyrimidinedione To a solution of 5-bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine (50 g) in dry tetrahydrofuran (11) at -78 C. was added n-butyllithium (69 ml of a 2.5M solution in hexanes) dropwise. After 0.5 hours, a solution of 5H-dibenzo[a,d]cyclohepten-5-one (44 g) in tetrahydrofuran (100 ml) was added. The reaction mixture was stirred at -78 C. for three hours and then allowed to warm to room temperature overnight. Saturated aqueous ammonium chloride solution (400 ml) was added and the mixture extracted with ethyl acetate. The organic solution was dried (MgSO4) and evaporated under reduced pressure to give the crude 5-(2,4-bis(1,1-dimethylethoxy)pyrimidin-5-yl)-5H-dibenzo[a,d]cyclohepten-5-ol which was used directly.

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. 19752-61-5, 5-Bromo-2,4-di-tert-butoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Astra Pharmaceuticals Limited; US6107297; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1211522-68-7, name is 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine

To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

The synthetic route of 1211522-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 640769-71-7, name is 2-(Pyrimidin-5-yl)benzaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-(Pyrimidin-5-yl)benzaldehyde

Tetrabutylammonium fluoride (TBAF, 0.1 ml of 1M in THF) was added to a solution of 2-pyrimidin-5-yl-benzaldehyde (184 mg, 1 mmol) and trifluoromethyl trimethylsilane (TMSCF3, 0.2 ml, 1.2 mmol) in 10 ml THF at 0 C. The mixture was warmed up to room temperature and stirred for 4 hours. The mixture was then treated with 3 ml of 1M HCl and stirred overnight. The product was extracted with ethyl acetate (3*20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 0.21 g of 2,2,2-trifluoro-1-(2-pyrimidin-5-yl-phenyl)-ethanol (yield: 84%), which was directly used in next step without purification.

With the rapid development of chemical substances, we look forward to future research findings about 640769-71-7.

Reference:
Patent; Jin, Haihong; Shi, Zhi-Cai; Tunoori, Ashok; Wang, Ying; Zhang, Chengmin; Devasagayaraj, Arokiasamy; US2008/153852; (2008); 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. 60703-46-0, name is 2,4,6-Trichloro-5-methoxypyrimidine, molecular formula is C5H3Cl3N2O, 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 2,4,6-Trichloro-5-methoxypyrimidine

10. Preparation of 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine 2,4,6-Trichloro-5-methoxypyrimidine (1.0 g, 4.7 mmol, see U.S. Pat. No. 3,984,411 for preparation) was dissolved in 15 mL dry dimethyl sulfoxide (DMSO) and treated with a stream of ammonia gas for 30 min. The mixture was poured into 30 mL water and the precipitated product was collected by filtration and washed with water. This solid was dissolved in 40 mL ethyl acetate, washed twice with water, washed once with brine, dried and evaporated to give the title compound (800 mg, 88% yield): mp 155-156 C.: 1H-NMR (DMSO-d6+D2O) delta 3.71 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 60703-46-0.

Reference:
Patent; Epp, Jeffrey B.; Schmitzer, Paul R.; Guenthenspberger, Katherine A.; Lo, William C.; Siddall, Thomas L.; US2009/62125; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 875251-47-1 , The common heterocyclic compound, 875251-47-1, name is 2-(Pyrimidin-5-yl)ethanol, molecular formula is C6H8N2O, 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 solution of 2-(pyrimidin-5-yl)ethan-1-ol in DCM was added SOC12 at 0 C and stirred at room temperature for 2 hours. Concentrated to afford the title compound as yellow oil. ?H-NMR (300 MHz, CDC13): oe 9.13 (s, 1H), 8.65 (s, 2H), 3.75 (t, 2H), 3.08 (t, 2H) ppm.

The synthetic route of 875251-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPITHERAPEUTICS APS; BOESEN, Thomas; LABELLE, Marc; YANG, Ying; SARASWAT, Neerja; DUDEKULA, Dastagiri; COOK, Cyril John; VAKITI, Ramkrishna Reddy; ZHANG, Rui; ULLAH, Farman; (316 pag.)WO2016/33169; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia