103686-53-9Relevant academic research and scientific papers
Development of a Practical Synthesis of a Pyrimidine Derivative with Fungicidal Activity
Ryan, Sarah J.,Yang, Qiang
, p. 2157 - 2165 (2019)
A scalable synthesis of a pyrimidine fungicide lead was developed. The pyrimidine head, 1-(5-bromopyridin-2-yl)-2,2-dimethyl-1-(pyrimidin-5-yl)propan-1-ol, was prepared by metal-halogen exchange of 2-iodo-5-bromopyridine with i-PrMgCl followed by treatment with pivaloyl chloride (PivCl) in the presence of CuCN·2LiCl and subsequent addition of 5-lithiopyrimidine. The boronic acid tail, (4-(1-cyanocyclobutyl)-2-fluorophenyl)boronic acid, was prepared via treatment of 1-(4-bromo-3-fluorophenyl)cyclobutane-1-carbonitrile with i-PrMgCl and trimethylborate. The o-fluoro Grignard reagent formed during this reaction sequence was analyzed by two-drop calorimetry and accelerating rate calorimetry, which revealed minimal safety concerns for scale-up. Finally, the boronic acid tail was coupled with the pyrimidine head in the presence of catalytic palladium acetate [Pd(OAc)2]/triphenylphosphine (PPh3) to deliver the final product in >95% yield after crystallization.
Process for the preparation of 5-acylpyrimidines
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, (2008/06/13)
A process for the preparation of a 5-acylpyrimidine of the formula STR1 in which R is an organic radical comprising reacting a methyl ketone of the formula in a first stage with a formylating reagent in the presence of a base to form an enolketone of the
