Studies on Pyrimidine Derivatives. XXXVIII.1) Cross-Coupling Reaction of N-Heteroaryl Iodides with Ethoxycarbonylmethylzinc Bromide in the Presence of Palladium Catalyst

Hiroshi Yamanaka; Masayuki Annaka; Yoshinori Kondo; Takao Sakamoto

doi:10.1248/cpb.33.4309

Studies on Pyrimidine Derivatives. XXXVIII.¹⁾ Cross-Coupling Reaction of N-Heteroaryl Iodides with Ethoxycarbonylmethylzinc Bromide in the Presence of Palladium Catalyst

Hiroshi Yamanaka, Masayuki Annaka, Yoshinori Kondo, Takao Sakamoto

PHA - Molecular Pharmaceutical Science

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

24 Citations (Scopus)

Abstract

In the presence of tetrakis(triphenylphosphine)palladium, 2-iodo-4,6-dimethylpyrimidine and 4-iodo-2,6-dimethylpyrimidine reacted with ethoxycarbonylmethylzinc bromide (Reformatsky reagent) to give ethyl 4,6-dimethyl-2-pyrimidineacetate and ethyl 2,6-dimethyl-4-pyrimidineacetate, respectively. In contrast, the reaction of 5-iodo-2,4-dimethylpyrimidine with the same reagent resulted in recovery of the starting iodide. Similar results were observed in the reactions of various N-heteroaryl iodides.

Original language	English
Pages (from-to)	4309-4313
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	33
Issue number	10
DOIs	https://doi.org/10.1248/cpb.33.4309
Publication status	Published - 1985 Jan 1

Keywords

N-hetero-arylacetic acid
N-heteroaryl halide
Reformatsky reagent
cross-coupling reaction
ethyl bromoacetate
palladium catalyst

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.33.4309

Cite this

Studies on Pyrimidine Derivatives. XXXVIII.¹⁾ Cross-Coupling Reaction of N-Heteroaryl Iodides with Ethoxycarbonylmethylzinc Bromide in the Presence of Palladium Catalyst. / Yamanaka, Hiroshi; Annaka, Masayuki; Kondo, Yoshinori et al.

In: Chemical and Pharmaceutical Bulletin, Vol. 33, No. 10, 01.01.1985, p. 4309-4313.

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

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abstract = "In the presence of tetrakis(triphenylphosphine)palladium, 2-iodo-4,6-dimethylpyrimidine and 4-iodo-2,6-dimethylpyrimidine reacted with ethoxycarbonylmethylzinc bromide (Reformatsky reagent) to give ethyl 4,6-dimethyl-2-pyrimidineacetate and ethyl 2,6-dimethyl-4-pyrimidineacetate, respectively. In contrast, the reaction of 5-iodo-2,4-dimethylpyrimidine with the same reagent resulted in recovery of the starting iodide. Similar results were observed in the reactions of various N-heteroaryl iodides.",

keywords = "N-hetero-arylacetic acid, N-heteroaryl halide, Reformatsky reagent, cross-coupling reaction, ethyl bromoacetate, palladium catalyst",

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AU - Sakamoto, Takao

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AB - In the presence of tetrakis(triphenylphosphine)palladium, 2-iodo-4,6-dimethylpyrimidine and 4-iodo-2,6-dimethylpyrimidine reacted with ethoxycarbonylmethylzinc bromide (Reformatsky reagent) to give ethyl 4,6-dimethyl-2-pyrimidineacetate and ethyl 2,6-dimethyl-4-pyrimidineacetate, respectively. In contrast, the reaction of 5-iodo-2,4-dimethylpyrimidine with the same reagent resulted in recovery of the starting iodide. Similar results were observed in the reactions of various N-heteroaryl iodides.

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