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Merck
  • Straightforward and highly efficient catalyst-free one-step synthesis of 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates, and 6-methylpurines through S(N)Ar-based reactions of 6-halopurines with ethyl acetoacetate.

Straightforward and highly efficient catalyst-free one-step synthesis of 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates, and 6-methylpurines through S(N)Ar-based reactions of 6-halopurines with ethyl acetoacetate.

Organic letters (2009-03-20)
Gui-Rong Qu, Zhi-Jie Mao, Hong-Ying Niu, Dong-Chao Wang, Chao Xia, Hai-Ming Guo
ABSTRACT

A novel approach to the synthesis of purines bearing functionalized carbon substituents or methyl in position 6 was developed. Under different reaction conditions, 6-halopurine derivatives could react with ethyl acetoacetate efficiently to yield 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates and 6-methylpurines respectively. No metal catalyst and ligand were required.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethyl acetoacetate, puriss. p.a., ≥99.0% (GC)
Sigma-Aldrich
Ethyl acetoacetate, natural, ≥97%, FG
Sigma-Aldrich
Ethyl acetoacetate, ReagentPlus®, 99%
Sigma-Aldrich
Ethyl acetoacetate, ≥99%, FCC, FG
Sigma-Aldrich
Ethyl acetoacetate, Arxada quality, ≥99.0% (GC)