928119-10-2

Upstream product

• 69207-36-9 ethyl 6-methyl-4-phenylpyrimidin-2(1H)-one-5-carboxylate 
• 108-95-2 phenol 
• 1095-03-0 triphenylborane 
• 123043-88-9 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 
• 74840-45-2 6-methyl-2-methylthio-4-phenyl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester 
• 113697-42-0 ethyl 4-methyl-2-(methylthio)-6-phenylpyrimidine-5-carboxylate 
• 1483-72-3 diphenyliodonium chloride 
• 66003-76-7 Diphenyliodonium triflate 
• 1245716-47-5 ethyl 4-methyl-6-phenyl-2-(tosyloxy)pyrimidine-5-carboxylate 

Relevant academic research and scientific papers

Oxidative Dehydrosulfurative Carbon-Oxygen Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Aryl Alcohols

A Pd-catalyzed/Cu-mediated oxidative dehydrosulfurative carbon-oxygen cross-coupling reaction of 3,4-dihydropyrimidin-1H-2-thiones (DHPMs) with aryl alcohols is described. Due to the ready availability of diverse DHPMs and aryl alcohols, the reaction method offers facile access to biologically and pharmacologically valuable 2-aryloxypyrimidine derivatives with rapid diversification.

Boric Ester and Thiourea as Coupling Partners in a Copper-Mediated Oxidative Dehydrosulfurative Carbon-Oxygen Cross-Coupling Reaction

A copper-mediated oxidative dehydrosulfurative carbon-oxygen cross-coupling reaction with boric ester and six-membered cyclic thiourea for single-step production of densely substituted 2-alkoxypyrimidines incorporated in a privileged scaffold is described. This is the first demonstration of boric ester acting as an alkoxy donor in a metal-catalyzed coupling reaction to produce ether. The reaction method offers a shortcut for producing 2-alkoxypyrimidine derivatives with rapid diversification and expands the utility of boric ester and the scope of Liebeskind-Srogl-type reactions.

C-O and C-S coupling reaction of 1,2-di(pyrimidin-2-yl) disulfides with phenols/thiophenols promoted by copper(I) chloride

An efficient protocol for C-O and C-S bonds formation by the cross-coupling reaction of 1,2-di(pyrimidin-2-yl) disulfides with phenols/thiophenols promoted by copper(I) chloride was established. It was discovered that variously substituted di(hetero)aryl disulfides and phenols were well tolerated. This strategy is the conversion of disulfides into hetero-aryl ethers and thioethers by a copper-promoted chemoselective C-S bond cleavage of disulfides.

Direct metal-free O-arylation of Biginelli 4-aryl-6-methyl-pyrimidine-2(1H)-one derivatives using diaryliodonium salts

4-Aryl-6-methyl-pyrimidine-2(1H)-one scaffolds of Biginelli type were subjected to C-O cross-coupling reactions using symmetrical diaryliodonium salts under transition metal-free conditions to afford 2-aryloxy pyrimidine derivatives in good to excellent y

Cross-coupling reactions of pyrimidin-2-yl sulfonates with phenols and anilines: An efficient approach to C2-functionalized pyrimidines

Pyrimidin-2-yl sulfonates, as an efficient reaction partner, which can be easily prepared from cheap commercial materials, were coupled with phenols and anilines to give a wide array of C2-aryloxy- and arylaminopyrimidines in good to excellent yields under mild reaction conditions. Copyright

Pd-catalyzed direct arylation of tautomerizable heterocycles with aryl boronic acids via C-OH bond activation using phosphonium salts

The first direct arylation via C-OH bond activation of tautomerizable heterocycles has been achieved using phosphonium salts, on the basis of a combination of the phosphonium coupling and Suzuki-Miyaura cross-coupling conditions. Optimal reaction condition is obtained through screening of phosphonium salts, Pd catalysts, and bases. The direct arylation via C-OH bond activation tolerates a variety of tautomerizable heterocycles and aryl boronic acids. The mechanism of the Pd-catalyzed phosphonium coupling is proposed to proceed via a domino seven-step process including the unprecedented heterocycle-Pd(II)-phosphonium species. Application of the Pd-catalyzed direct arylation via C-OH bond activation using PyBroP leads to the most efficient synthesis of the biologically important 6-arylpurine ribonucleoside in a single step from unactivated and unprotected inosine. Copyright