90210-57-4

Upstream product

• 1722-12-9 2-chloropyrimidine 
• 1224-56-2 tributylbenzylphosphonium chloride 
• 1589-82-8 phenylmagnesium bromide 
• 14080-19-4 2-(methylsulfinyl)pyrimidine 
• 112170-35-1 α-phenyl-2-pyrimidinylacetonitrile 
• 90210-54-1 2-Benzyl-pyrimidine 1-oxide 
• 14080-22-9 phenyl 2-pyrimidinyl sulfoxide 
• 6921-34-2 benzylmagnesium chloride 
• 25099-79-0 2-benzyl-1,4,5,6-tetrahydropyrimidine 
• 823-09-6 2-(methylsulfanyl)pyrimidine 
• 62673-31-8 benzyl(bromo)zinc 
• 140-29-4 phenylacetonitrile 
• 103-82-2 phenylacetic acid 

Downstream Products

• 774-65-2 benzoic acid tert-butyl ester 
• 1581709-78-5 2-(1-phenylvinyl)pyrimidine 
• 112170-34-0 phenyl(pyrimidin-2-yl)methanone 
• 90210-54-1 2-Benzyl-pyrimidine 1-oxide 

Relevant academic research and scientific papers

A VERSATILE LIGAND FOR PALLADIUM-CATALYZED META-C-H FUNCTIONALIZATIONS

A class of mono-protected 3-amino-2- hydroxypyridine (MPAHP) ligands that enable the meta- C-H arylation of anilines, phenols, phenylacetic acids, and biologically relevant heterocyclic compounds using norbornene as a transient mediator is disclosed. The applicability of this meta-arylation methodology in the pharmaceutical industry is illustrated for heteroaryl substrates and heteroaryl iodide coupling partners, a feat made possible by using the MPAHP ligand. The enabling nature of MPAHP ligands to achieve other meta-C-H functionalization processes is also illustrated by the development of a meta-C-H amination reaction and a meta-C-H alkynylation reaction.

Palladium-catalyzed direct arylation of aryl(azaaryl)methanes with aryl halides providing triarylmethanes

Direct arylation of aryl(azaaryl)methanes with aryl halidas takes place at the benzylic position in the presence of a hydroxide base under palladium catalysis to yield triarylmethanes

Palladium-catalyzed cross-coupling of benzylzinc reagents with methylthio N-heterocycles: A new coupling reaction with unusual selectivity

Benzylzinc reagents undergo palladium-catalyzed cross-coupling reactions with methylthio-substituted N-heterocycles in moderate to good yields. 2- (Methylthio)pyrimidines are particularly reactive substrates for this reaction. As a result, the regioselectivity of 2,4-bis(methylthio)pyrimidines is opposite to that of their 2,4-dichloropyrimidine analogues. This unusual cross-coupling reaction offers new flexibility in the regioselective synthesis of substituted pyrimidines and other heterocycles.

Ligand coupling reactions of 2-pyridyl, 4-pyridyl and 2-pyrimidyl sulfoxides with grignard reagents

The ligand coupling reaction was extended to 3-and 4-pyridyl sulfoxides as well as the 2-pyrimidyl moiety with Grignard reagents. It was found that both 4-pyridyl and 2-pyrimidyl sulfoxides nicely underwent the ligand coupling reactions, but 3-pyridyl sulfoxide underwent ligand exchange.

Preparation of Heteroaryl Phenylmethanes and a 13C and 15N NMR Spectroscopic Study of their Conjugate Carbanions. Rotational Isomerism and Charge Maps of the Anions and Ranking of the Charge Demands of the Heterocycles

2-Benzylpyridazine, 4-benzylpyrimidine, 2-benzylpyrimidine and 2-benzylpyrazine, (5-8) have been prepared in order to study their 13C and 15N spectra and those of their conjugate carbanions (1-4).These systems are aza-homologues of the previously reported

FORMATION OF PHENYL SUBSTITUTED HETEROAROMATICS BY LIGAND COUPLING IN THE REACTION BETWEEN HETEROARYL SULFOXIDES WITH PHENYL GRIGNARD REAGENT

In the reaction of heteroaryl alkyl sulfoxides with phenylmagnesium bromide, phenyl group was found to couple predominantly with 2-quinolyl group and 2-pyrimidinyl group.

SYNTHESIS OF 2-ALKYLPYRIMIDINES VIA 2-ALKYL-1,4,5,6-TETRAHYDROPYRIMIDINES

The condensation of 1,3-diaminopropane with alkanoic acids gives 2-alkyl-1,4,5,6-tetrahydropyrimidines.Dehydrogenation of the tetrahydropyrimidine derivatives over a palladium catalyst produces the 2-alkylpyrimidines in high yields.

OCCURRENCE OF LIGAND COUPLING IN THE REACTIONS OF VARIOUS SULFOXIDES WITH GRIGNARD REAGENTS

Ligand coupling reactions take place not only between benzyl and 2-pyridyl groups and two 2-pyridyl groups in the treatment of benzyl, alkyl and aryl 2-pyridyl sulfoxides with Grignard reagents, but also between such groups as p-benzenesulfonylphenyl, 4-pyridyl, 2-quinolyl and 2-pyrimidyl, and the benzyl group.There are cases in which ligand exchange precedes ligand coupling, especially with 2-heteroaryl groups.In addition, even some alkyl groups were found to couple with the 2-pyridyl group.The ease of coupling seems to be associated with the electronegativity of the coupling carbon atom of the ligand, when one compares the 13C NMR chemical shifts.