80742-17-2

Basic information

• Product Name: 5-Pyrimidinecarboxylic acid, 4-methyl-2,6-diphenyl-, ethyl ester
• CAS NO: 80742-17-2
• Molecular Formula: C20H18N2O2
• Molecular Weight: 318.375
• Mol File: 80742-17-2.mol

Chemical Properties

• CAS DataBase Reference: 5-Pyrimidinecarboxylic acid, 4-methyl-2,6-diphenyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Pyrimidinecarboxylic acid, 4-methyl-2,6-diphenyl-, ethyl ester(80742-17-2)
• EPA Substance Registry System: 5-Pyrimidinecarboxylic acid, 4-methyl-2,6-diphenyl-, ethyl ester(80742-17-2)

Safety Data

• Hazardous Substances Data: 80742-17-2(Hazardous Substances Data)

Upstream product

• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 80742-09-2 (2S,4R)-6-Methyl-2,4-diphenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 
• 69207-36-9 ethyl 6-methyl-4-phenylpyrimidin-2(1H)-one-5-carboxylate 
• 98-80-6 phenylboronic acid 
• 1421829-18-6 ethyl 4-methyl-6-phenyl-2-(phenylthio)pyrimidine-5-carboxylate 
• 100-58-3 phenylmagnesium bromide 
• 591-50-4 iodobenzene 
• 36746-07-3 2-chloro-4-methyl-6-phenylpyrimidine-5-carboxylic acid ethyl ester 
• 2996-92-1 phenyl trimethylsiloxane 
• 113697-42-0 ethyl 4-methyl-2-(methylthio)-6-phenylpyrimidine-5-carboxylate 
• 123043-88-9 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 
• 108-86-1 bromobenzene 
• 1245716-47-5 ethyl 4-methyl-6-phenyl-2-(tosyloxy)pyrimidine-5-carboxylate 
• 1606128-40-8 C₁₉H₁₇N₃O₂S₂ 

Downstream Products

• 21829-26-5 diethyl 4-(2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 80742-12-7 ethyl (2RS,4SR)-6-methyl-2,4-bis(2-nitrophenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 80742-12-7 ethyl (2RS,4RS)-6-methyl-2,4-bis(2-nitrophenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate 

Relevant articles and documents

Palladium-catalyzed Hiyama cross-couplings of 2-chloro pyrimidines with organosilanes

An efficient synthesis of C2-aryl pyrimidine derivatives via Pd-catalyzed Hiyama couplings has been developed. Various 2-chloro pyrimidines with electron-donating or electron-withdrawing groups as novel electrophile partners coupled well with trimethoxy(p

Palygorskite-anchored Pd complexes catalyze the coupling reactions of pyrimidin-2-yl sulfonates

In this work, an anchored Pd complex (PGS-APTES-Pd(OAc)2) was prepared via simple and green steps from the natural clay mineral palygorskite and was well characterized by XPS, XRD, IR, SEM, and EDX. This complex was further utilized as a fine catalyst for the C-C/C-N coupling reactions of pyrimidin-2-yl sulfonates. Subsequently, the cyclic utilization test indicated the high stability and sustainability of this PGS-APTES-Pd(OAc)2 catalyst, and no activation was required in the recycling process, providing an applicable and reusable catalyst in organic synthesis.

Palladium-Catalyzed Copper-Promoted Hiyama-Type Carbon-Carbon Cross-Coupling Reactions of Dihetaryl Disulfides as Electrophiles

Dihetaryl disulfides were used as electrophiles in a palladium-catalyzed carbon-carbon cross-coupling reaction with arylsilanes to realize a Hiyama-type reaction. This unique transformation shows high reactivity, excellent functional-group tolerance, and mild reaction conditions, making it an attractive alternative to conventional cross-coupling approaches for carbon-carbon bond construction.

Dehydrosulfurative arylation with concomitant oxidative dehydrogenation for rapid access to pyrimidine derivatives

This report describes a cascade reaction method for the synthesis of 2-arylpyrimidine derivatives via dehydrosulfurative carbon-carbon cross-coupling and concomitant oxidative dehydrogenation under a Pd/Cu catalytic system. It provides rapid and general access to a diverse range of 2-arylpyrimidines in a single step from a wide range of 3,4-dihydropyrimidin-1H-2-thiones (DHPMs) and arylboronic acids.

Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Bromides with Pyrimidin-2-yl Tosylates

A new protocol for the NiCl2-catalyzed cross-electrophile coupling of aryl bromides with pyrimidin-2-yl tosylates to give the corresponding C2-arylation pyrimidine derivatives has been developed. This study provides an improvement over previous methods by using pyrimidin-2-yl tosylates instead of halides as coupling partners that are stable and easily available.

Iron-catalyzed cross-coupling of heteroaromatic tosylates with alkyl and aryl Grignard reagents

An Fe(III)-catalyzed cross-coupling of N-heteroaromatic tosylates with aryl and alkyl Grignard reagents is presented. The reaction proceeds at -20°C to room temperature with short reaction time (15-30 min.), and the corresponding products are obtained with moderate to high yields. In particular, low-cost and abundantly available FeCl3 or Fe(acetylacetonate)3 catalyze the reaction without other special ligands. All tested N-heteroaromatic tosylates that are available including pyridine and pyrimidine derivatives were subject to the reaction, resulting in the expected products.

Ni-catalyzed Suzuki-Miyaura coupling reactions of pyrimidin-2-yl phosphates, tosylates and pivalates with arylboronic acids

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 to

Wool-anchored Pd(OAc)2 complex: A highly active and reusable catalyst for desulfurative coupling reactions

A biomacromolecule-anchored palladium complex, wool-Pd(OAc)2, was prepared and characterized by IR, XPS, SEM and ICP. The new complex was used as a catalyst for the Liebeskind-Srogl desulfurative coupling reactions of pyrimidin-yl thioether derivatives with terminal alkynes and aryl boronic acids. Products were isolated in moderate to excellent yields. When 2-(phenylthio)-1,4-dihydropyrimidine derivatives were reacted with terminal alkynes and carboxyl acids, a domino reaction process was revealed. In these reactions, this novel and efficient catalyst was capable of being reused for at least nine rounds, with durable performance and wide substrate tolerance.

Chemo-controlled cross-coupling of Di(hetero)aryl disulfides with grignard reagents: C-C vs. C-S bond formation

A general protocol for the chemoselectivity-controlled C-C and C-S coupling reactions of di(hetero)aryl disulfides with Grignard reagents catalyzed by ferrocene and palladium acetate has been developed. Ferrocene favored the formation of C-S coupled products at low temperature, whereas C-C bond couplings were favored when palladium acetate was used. All the reactions proceeded with excellent chemoselectivity and in good yields under mild conditions, and a library of molecules with pyridine and pyrimidine scaffolds was produced.

RETRACTED ARTICLE: Reusable biomacromolecule-Pd complex catalyzed C-C cross-coupling reactions via C-S cleavage of disulfides

A well-defined heterogeneous palladium catalyst, natural wool supported Pd(OAc)2-complex was found to be an effective catalyst for the C-S bonds cleavage and C-C bonds formation from 1,2-di(pyrimidin-2-yl)disulfane derivatives with arylboronic acids or terminal alkynes, giving the desired coupling products in moderate to excellent yields. The novel catalyst, which is stable and easy handling in experiment, was characterized by XPS, IR, SEM and ICP analysis. Subsequent analysis of the used catalyst after reaction revealed its negligible metal leaching and at least 10 rounds of recycled catalyzing capacity and wide range of substrate tolerance.