54095-18-0

Upstream product

• 14774-77-7 p-methoxyphenyllithium 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 17758-33-7 3-methyl-5-nitro-4(3H)-pyrimidinone 
• 768-60-5 4-methoxyphenylacetylen 
• 96155-57-6 1-(4-methoxyphenyl)ethanone O-acetyl oxime 
• 149-73-5 trimethyl orthoformate 
• 2475-92-5 4-methoxyacetophenone oxime 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 30680-61-6 pyrimidine hydrochloride 
• 289-95-2 PYRIMIDINE 
• 100-66-3 methoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 18096-70-3 3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one 
• 3473-63-0 formamidine acetic acid 

Downstream Products

• 868548-64-5 6,6'-bis(p-methoxyphenyl)-4,4'-bipyrimidine 
• 1357585-23-9 C₂₄H₂₀N₂O₄ 
• 883822-72-8 C₂₅H₂₂N₂O₅ 
• 887407-76-3 6-(4-methoxyphenyl)pyrimidine-4-carboxylic acid 

Relevant academic research and scientific papers

Direct C-H photoarylation of diazines using aryldiazonium salts and visible-light

In this study, direct C-H photoarylation of pyrazine with aryldiazonium salts under visible-light irradiation (blue-LEDs) is described, and additional examples including photoarylations of pyrimidine and pyridazine are also covered. The corresponding aryl-diazines were prepared in yields up to 84% only by mixing and irradiating the reaction with no need for an additional photocatalyst. We demonstrate the efficacy of this protocol by the scope with electron-donor, -neutral, and -withdrawing groups attached at the ortho, meta, and para positions of the aryldiazonium salts; the results are better than those reported for ruthenium-complex mediated photoarylations. Additionally, we demonstrate the robustness of this methodology with a 5 mmol scaled-up experiment. Mechanistic studies were carried out giving support to the proposal of a photocatalyzed approach by an electron donor-acceptor (EDA) complex, also highlighting the crucial role that solvents play in the formation of the EDA complex. This journal is

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.

Atom- and step-economical nucleophilic arylation of azaaromatics: Via electrochemical oxidative cross C-C coupling reactions

The synthesis of asymmetrical bi(het)aryls through direct functionalization of the C(sp2)-H bond in azaaromatics with fragments of (hetero)aromatic nucleophiles has first been carried out under electrochemical oxidative conditions. This versati

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, and docking studies of phenylpyrimidine-carboxamide derivatives bearing 1H-pyrrolo[2,3-b]pyridine moiety as c-Met inhibitors

Four series of phenylpyrimidine-carboxamide derivatives bearing 1H-pyrrolo[2,3-b]pyridine moiety (14a-e, 15a-g, 16a-e and 17a-g) were designed, synthesized and evaluated for the IC50 values against three cancer cell lines (A549, PC-3 and MCF-7). Four selected compounds (15e, 16a-b and 17a) were further evaluated for the activity against c-Met kinase, HepG2 and Hela cell lines. Most of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 valuables in single-digit μM to nanomole range. Eleven of them are equal to more active than positive control Foretinib against one or more cell lines. The most promising compound 15e showed superior activity to Foretinib against A549, PC-3 and MCF-7 cell lines, with the IC50 values of 0.14 ± 0.08 μM, 0.24 ± 0.07 μM and 0.02 ± 0.01 μM, which were 4.6, 1.6 and 473.5 times more active than Foretinib (0.64 ± 0.26 μM, 0.39 ± 0.11 μM, 9.47 ± 0.22 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the replacement of phenylpicolinamide scaffold with phenylpyrimidine fragment of the target compounds was benefit for the activity. What's more, the introduction of fluoro atom to the aminophenoxy part played no significant impact on the activity and any substituent group on aryl group is unfavourable for the activity.

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.

Direct arylation of n-heteroarenes with aryldiazonium salts by photoredox catalysis in water

A highly effective visible light-promoted "radical-type" coupling of N-heteroarenes with aryldiazonium salts in water has been developed. The reaction proceeds at room temperature with [Ru(bpy)3]Cl 2×6 H2O as a photosensit

One-pot and three-component synthesis of substituted pyrimidines catalysed by boron sulfuric acid under solvent-free conditions

An efficient, simple and one-pot synthesis of pyrimidine derivatives by a three-component reaction of ketones, triethyl orthoformate, and ammonium acetate in the presence of boron sulfuric acid as a reusable and efficient catalyst under solvent-free conditions is reported. The reusability of catalyst, simplicity of the starting materials, short reaction time, one-pot, and good yields of products are the main advantages.

One-pot synthesis of pyrimidines under solvent-free conditions

N,N,N',N'-Tetrabromobenzene-1,3-disulfonamide was used as an efficient catalyst for the one-pot synthesis of pyrimidine derivatives in excellent yields from triethoxymethane, ammonium acetate, and various ketone derivatives at 100-110 °C under solvent-fre

Efficient one-pot, three-component synthesis of a library of pyrrolo[1,2-c]pyrimidine derivatives

Herein is reported a simple and efficient one-pot three-component synthesis of pyrrolo[1,2-c]pyrimidine derivatives starting from various substituted pyrimidines, 2-bromoacetophenones, and electron deficient alkynes in epoxides acting both as reaction medium and HBr scavanger. This method proved to be very lucrative and avoids formation of ylide inactivation products. The synthesis represents an environmentally benign alternative to classical methods. The new library of compounds was briefly characterized regarding the improved Lipinski rule to asses the potential drug-likeness of the compounds. The majority of compounds are statisfing the Lipinski rule.