Studies on Pyrimidine Derivatives. XXVIII. Synthesis of Pyridopyrimidine Derivatives by Cross-coupling of Halopyrimidines with Olefins and Acetylenes

Takao Sakamoto; Yoshinori Kondo; Hiroshi Yamanaka

doi:10.1248/cpb.30.2410

Studies on Pyrimidine Derivatives. XXVIII. Synthesis of Pyridopyrimidine Derivatives by Cross-coupling of Halopyrimidines with Olefins and Acetylenes

Takao Sakamoto, Yoshinori Kondo, Hiroshi Yamanaka

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

Abstract

Three kinds of pyridopyrimidines were synthesized from appropriate pyrimidine derivatives. Cross-coupling of 4-amino-5-iodopyrimidines with α,β-unsaturated carboxylic esters followed by ring-closure afforded pyrido[2,3-d]pyrimidines. Ammonolysis of 4-ethoxycarbonyl-5-phenylethynyl- and 5-ethoxycarbonyl-4-phenylethynyl-pyrimidines which were obtained by cross-coupling of the corresponding halopyrimidines with phenylacetylene, gave pyrido[3,4-d]- and pyrido[4,3-d]-pyrimidines, respectively.

Original language	English
Pages (from-to)	2410-2416
Number of pages	7
Journal	Chemical and Pharmaceutical Bulletin
Volume	30
Issue number	7
DOIs	https://doi.org/10.1248/cpb.30.2410
Publication status	Published - 1982 Jan 1

Keywords

5-iodopyrimidine
ethyl 5-pyrimidineacrylate
palladium-catalyzed cross-coupling reaction
phenylethynylpyrimidine
pyridopyrimidine
ring-closure reaction
styrylpyrimidine

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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title = "Studies on Pyrimidine Derivatives. XXVIII. Synthesis of Pyridopyrimidine Derivatives by Cross-coupling of Halopyrimidines with Olefins and Acetylenes",

abstract = "Three kinds of pyridopyrimidines were synthesized from appropriate pyrimidine derivatives. Cross-coupling of 4-amino-5-iodopyrimidines with α,β-unsaturated carboxylic esters followed by ring-closure afforded pyrido[2,3-d]pyrimidines. Ammonolysis of 4-ethoxycarbonyl-5-phenylethynyl- and 5-ethoxycarbonyl-4-phenylethynyl-pyrimidines which were obtained by cross-coupling of the corresponding halopyrimidines with phenylacetylene, gave pyrido[3,4-d]- and pyrido[4,3-d]-pyrimidines, respectively.",

keywords = "5-iodopyrimidine, ethyl 5-pyrimidineacrylate, palladium-catalyzed cross-coupling reaction, phenylethynylpyrimidine, pyridopyrimidine, ring-closure reaction, styrylpyrimidine",

author = "Takao Sakamoto and Yoshinori Kondo and Hiroshi Yamanaka",

year = "1982",

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doi = "10.1248/cpb.30.2410",

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T1 - Studies on Pyrimidine Derivatives. XXVIII. Synthesis of Pyridopyrimidine Derivatives by Cross-coupling of Halopyrimidines with Olefins and Acetylenes

AU - Sakamoto, Takao

AU - Kondo, Yoshinori

AU - Yamanaka, Hiroshi

PY - 1982/1/1

Y1 - 1982/1/1

N2 - Three kinds of pyridopyrimidines were synthesized from appropriate pyrimidine derivatives. Cross-coupling of 4-amino-5-iodopyrimidines with α,β-unsaturated carboxylic esters followed by ring-closure afforded pyrido[2,3-d]pyrimidines. Ammonolysis of 4-ethoxycarbonyl-5-phenylethynyl- and 5-ethoxycarbonyl-4-phenylethynyl-pyrimidines which were obtained by cross-coupling of the corresponding halopyrimidines with phenylacetylene, gave pyrido[3,4-d]- and pyrido[4,3-d]-pyrimidines, respectively.

AB - Three kinds of pyridopyrimidines were synthesized from appropriate pyrimidine derivatives. Cross-coupling of 4-amino-5-iodopyrimidines with α,β-unsaturated carboxylic esters followed by ring-closure afforded pyrido[2,3-d]pyrimidines. Ammonolysis of 4-ethoxycarbonyl-5-phenylethynyl- and 5-ethoxycarbonyl-4-phenylethynyl-pyrimidines which were obtained by cross-coupling of the corresponding halopyrimidines with phenylacetylene, gave pyrido[3,4-d]- and pyrido[4,3-d]-pyrimidines, respectively.

KW - 5-iodopyrimidine

KW - ethyl 5-pyrimidineacrylate

KW - palladium-catalyzed cross-coupling reaction

KW - phenylethynylpyrimidine

KW - pyridopyrimidine

KW - ring-closure reaction

KW - styrylpyrimidine

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Studies on Pyrimidine Derivatives. XXVIII. Synthesis of Pyridopyrimidine Derivatives by Cross-coupling of Halopyrimidines with Olefins and Acetylenes

Abstract

Keywords

ASJC Scopus subject areas

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