68049-19-4

Basic information

• Product Name: Pyrimidine, 4-(4-fluorophenyl)- (9CI)
• Synonyms: Pyrimidine, 4-(4-fluorophenyl)- (9CI);4-(4-Fluorophenyl)pyrimidine
• CAS NO: 68049-19-4
• Molecular Formula: C₁₀H₇FN₂
• Molecular Weight: 174.1743832
• Product Categories: PYRIMIDINE;QUINAZOLINE
• Mol File: 68049-19-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyrimidine, 4-(4-fluorophenyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimidine, 4-(4-fluorophenyl)- (9CI)(68049-19-4)
• EPA Substance Registry System: Pyrimidine, 4-(4-fluorophenyl)- (9CI)(68049-19-4)

Safety Data

• Hazardous Substances Data: 68049-19-4(Hazardous Substances Data)

Upstream product

• 3473-63-0 formamidine acetic acid 
• 138716-20-8 (E)-3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 6966-73-0 triformylaminomethane 
• 122-51-0 orthoformic acid triethyl ester 
• 290-87-9 1,3,5-Triazine 
• 75175-77-8 3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 77287-34-4 formamide 
• 329-79-3 1-(4-fluorophenyl)ethanone oxime 
• 896885-34-0 1-(4-fluorophenyl)ethan-1-one-O-acetyl oxime 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1491142-21-2 4-(4-fluorophenyl)pyrimidine-2-carboxylic acid 
• 1491142-25-6 N-[3-fluoro-4-[[6-methoxy-7-[3-(4-morpholinyl)propoxy]quinoline-4-yl]oxy]phenyl]-4-(4-fluorophenyl)pyrimidine-2-carboxamide 
• 1491142-29-0 N-[3-fluoro-4-[[6-methoxy-7-[3-(1-piperidinyl)propoxy]quinoline-4-yl]oxy]phenyl]-4-(4-fluorophenyl)pyrimidine-2-carboxamide 
• 1491142-32-5 N-[3-fluoro-4-[[6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]quinoline-4-yl]oxy]phenyl]-4-(4-fluorophenyl)pyrimidine-2-carboxamide 
• 1491142-36-9 N-[3-fluoro-4-[[6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]quinoline-4-yl]oxy]phenyl]-4-(4-fluorophenyl)pyrimidine-2-carboxamide 
• 1491142-18-7 4-(4-fluorophenyl)pyrimidine-2-carboxamide 
• 1566622-52-3 C₂₂H₁₅FN₂O₂ 
• 302912-53-4 C₂₃H₁₇FN₂O₃ 
• 883822-18-2 C₂₄H₁₉FN₂O₄ 
• 1566622-54-5 C₂₂H₁₄F₂N₂O₂ 
• 1566622-59-0 C₂₂H₁₄F₂N₂O₃ 
• 302912-54-5 C₂₃H₁₆F₂N₂O₃ 
• 1566622-60-3 C₂₂H₁₄ClFN₂O₂ 
• 1566622-64-7 C₂₂H₁₄ClFN₂O₃ 

Relevant articles and documents

Catalyst free synthesis of mono- and disubstituted pyrimidines from O-acyl oximes

Transition-metal or iodine catalyzed transformations of O-acyl oximes to various N-heterocycles are well established. Herein, we report a catalyst free, oxime carboxylate based, three-component condensation method to access mono- and disubstituted pyrimidines. A broad range of substituted pyrimidines were prepared in moderate to excellent yields. Control experiments reveal that in situ generated formamidine is the key intermediate.

Pd-catalyzed decarboxylative cross-coupling of sodium pyrimidinecarboxylates with (hetero)aryl bromides

A straightforward method for the synthesis of functionalized 4- or 5-(hetero)arylpyrimidines via decarboxylative cross-coupling reaction from readily available pyrimidine-4- and pyrimidine-5-carboxylates was described. In the presence of dual-catalyst system of Pd(PPh3)4/Cu2O, the reaction proceeds smoothly, tolerates a variety of functional groups, and provides easy access to the synthesis of different (hetero)arylpyrimidines compounds.

Synthesis, activity and docking studies of phenylpyrimidine–carboxamide Sorafenib derivatives

Two series of Sorafenib derivatives bearing phenylpyrimidine–carboxamide moiety (16a–g and 17a–p) were designed, synthesized and evaluated for the IC50values against three cancer cell lines (A549, MCF-7 and PC-3). Two selected compounds (17f and 17n) were further evaluated for the activity against VEGFR2/KDR kinase. More than half of the synthesized compounds showed moderate to excellent activity against three cancer cell lines. Compound 17f showed equal activity to Sorafenib against MCF-7 cell line, with the IC50values of 6.35 ± 0.43 μM. Meanwhile, compound 17n revealed more active than Sorafenib against A549 cell line, with the IC50values of 3.39 ± 0.37 μM. Structure–activity relationships (SARs) and docking studies indicated that the second series (17a–p) showed more active than the first series (16a–g). What's more, the introduction of fluoro atom to the phenoxy part played no significant impact on activity. In addition, the presence of electron-donating on aryl group was benefit for the activity.