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C2‐functionalized pyrimidine derivative is a family of important nitrogen heterocyclic compounds due to their unique structure and multiple reaction sites. In this work, a novel method for the synthesis of C2‐functionalized pyrimidine derivatives through phenylalkynes and pyrimidine disulfides under ambient conditions is proposed. The reaction can be triggered by adding catalytic amounts of cesium fluoride, which is characterized by free‐catalyst and special activator. Importantly, this reaction has good compatibility with substrates substituted by electron‐donating and electron‐withdrawing groups at C4. Density functional theory (DFT) calculations also indicates that the production of C2‐functionalized pyrimidine derivatives is more favourable. [ABSTRACT FROM AUTHOR]

This report describes the oxidative coupling reaction of dithiopyrimidines with phenylhydrazine hydrochlorides to synthesize a series of arylthiopyrimidine derivatives. The reaction does not require transition metals as catalysts, and uses organic dye rose bengal as photocatalyst and air as oxidant. The reaction conditions are mild and meet the requirements of green chemistry. In addition, the method has a wide scope of substrates and good tolerance of functional groups. The control experiment showed that the reaction may be a free radical mechanism, and the molecular weight of the intermediate was captured by high‐resolution mass spectrometry. [ABSTRACT FROM AUTHOR]

Pyrimidin-2-yl sulfonate, as an efficient reaction partner, can be easily prepared from cheap commercial materials, reacted with sodium azide and alkynes to give C2-triazolo functionalized pyrimidines in good yields under mild reaction conditions. This procedure eliminates the need to handle organic halides or organic azides, as they are generated in situ, making this already powerful click process even more user-friendly and safe. [ABSTRACT FROM AUTHOR]

Iron-catalyzed Kumada cross-coupling reactions of pyrimidin-2-yl phosphates and Grignard reagents are described. The reaction proceeds at room temperature with a short reaction time of 15 minutes, and the corresponding products are obtained with moderate to high yields. A wide array of C2-functionalized pyrimidines has been prepared in moderate to good yields and many functional groups are well tolerated. [ABSTRACT FROM AUTHOR]

The 4-arylated pyrimidin-2-yl tosylate derivatives, easily prepared from cheap commercial materials, reacted efficiently with propargyl alcohol/NaOBut to give the corresponding 4-arylated 2-propargyloxy-pyrimidine derivatives which, in a one-pot reaction catalysed by CuSO4·5H2O/sodium ascorbate, reacted with NaN3 and hexyl or benzyl bromide to give a series of 2-(1-hexyl- or 1-benzyl-1,2,3-triazol-4-yl)methoxy-pyrimidine derivatives in good yields. [ABSTRACT FROM AUTHOR]

New 2-(1,2,3-triazol-1-yl)pyrimidines were synthesized in good yields by the three-component reaction of pyrimidin-2-yl sulfonates, sodium azide and active methylene ketones in the presence of K2CO3 at room temperature. This procedure eliminates the need to handle organic azides in the synthesis of analogous compounds. [ABSTRACT FROM AUTHOR]

Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)2-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized. [ABSTRACT FROM AUTHOR]

Novel thiazolo[2,3- b]quinazolines were prepared by the cyclization reaction between octahydroquinazoline-2-thiones with α-bromoketones, which provides a readily accessible multifunctionalized quinazoline template for diversity-oriented synthesis. [ABSTRACT FROM AUTHOR]

Abstract: The Biginelli 3,4-dihydropyrimidin-2(1H)-one was converted to various C2-multifunctionalized pyrimidines via the dehydrogenation and Mitsunobu reaction using amines, alcohols, phenols and carboxylic acids as nucleophiles. A possible mechanism was also proposed to rationalize the formation of products. [Copyright &y& Elsevier]

A mild and rapid procedure to the synthesis of 2-substituted pyrimidines was developed via sequential functionalization of easily available Biginelli 3,4-dihydropyrimidine-2(1 H)-ones via oxidation, esterification, followed by cross-coupling reaction of ?pyrimidin-2-yl sulfonates with N, S, and O nucleophiles in PEG-400 as a green reaction medium at room temperature. [ABSTRACT FROM AUTHOR]

An abstract of the study "Palladium Catalyzed Mizoroki-Heck Reaction of Pyrimidin-2-yl Tosylates with Aromatic and Aliphatic Olefins" is presented.

Ni-catalyzed Suzuki–Miyaura cross-coupling reactions of pyrimidin-2-yl phosphates, tosylates and pivalates with arylboronic acids were described. A wide array of functionalized pyrimidines have been prepared in impressive yields and show good tolerance towards wide substrate scope. [ABSTRACT FROM AUTHOR]

(2-Chlorobenzoyloxy)copper(I) exhibited high activity towards the challenging amination of 2-amino pyrimidines with aryl halides. Herein, secondary and tertiary amines were selectively produced by using potassium phosphate and sodium- t -butoxide. Potassium phosphate favored the formation of secondary amines, whereas tertiary amines were favored when sodium- t -butoxide was used. [ABSTRACT FROM AUTHOR]

Abstract: A domino S–N and C–N coupling/oxidative aromatization process to synthesize 2-aminothio-phenylpyrimidines and 2-amino-phenylpyrimidines by S–N and C–N cross-coupling reactions is described. This methodology couples 3,4-dihydropyrimidine-2-thiones and secondary amines catalyzed by molecular iodine. Remarkably the C–N coupled product was obtained via a desulfitative coupling-aromatization reaction in one-pot reaction. [Copyright &y& Elsevier]

Abstract: N-Alkoxymethylation of heterocyclic compounds with diethyl phosphite via cleavage of P–O bond was investigated and a series of N3-ethoxymethylated heterocyclic compounds were synthesized. A mechanism in which diethyl phosphite acts as an efficient surrogate of ethanol was proposed and supported by several evidences. [Copyright &y& Elsevier]

Abstract: Polymer bound sulfonic acid was prepared on polystyrene–poly(ethylene glycol) (PS–PEG) resin. The PS–PEG-bound sulfonic acid exhibited good catalytic activity in the Biginelli-type reaction for the synthesis of 3,4-dihydropyrimidinones with good yield and good recyclability (six times). This method presents a remarkable technique toward an efficient synthesis of 3,4-dihydropyrimidinones. [Copyright &y& Elsevier]

A protocol for chemoselective transformation of disulfides into aryl and alkyl amines is developed. [ABSTRACT FROM AUTHOR]

The chemical structure for the three-component reaction of the compound pyrimidin-2-yl sulfonates with sodium azide and alkynes is presented, focusing on the approach to C2-triazolo functionalized pyrimidines.

A diagram is presented on 4-aryl-pyrimidin-2-yl tosylates (I) partners and synthesis of pyrimidines.

It is found that potassium phosphate used as base favors the formation of secondary amines (III), (VI), whereas tertiary amines (IV),(VII) are obtained when tBuONa is used. [ABSTRACT FROM AUTHOR]

The article presents chemical equations for article "Palladium(II) Catalyzed Suzuki/Sonogashira Cross-Coupling Reactions of Sulfonates: An Efficient Approach to C2-Functionalized Pyrimidines and Pyridines" by Z-J Quan and others, published in periodical "European Journal of Organic Chemistry in 2013.