Journal of Organic Chemistry p. 2391 - 2395 (1991)
Update date:2022-08-03
Topics:
Reynolds, Robert C.
Trask, Todd W.
Sedwick, W. David
The synthesis of 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine is described.Synthetically, this novel o-carboranyl pyrimidine is approached from ethyl 2-acetyl-4-pentynoate through alkylation of ethyl acetoacetate with propargyl bromide and subsequent condensation with thiourea to yield 6-methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone.Hydrolysis of the 2-thione and chlorination wirh POCl3 gives 2,4-dichloro-6-methyl-5-(2-propynyl)pyrimidine.Gentle refluxing of this product with B10H14/CH3CN in toluene yields the target, 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine, a potential synthon for a variety of 2,4-substituted 5-(1-o-carboranylmethyl)-6-methylpyrimidines and/or the corresponding nido-undecaborates.
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