2,4-DICHLORO-5-(1-ORTHO-CARBORANYLMETHYL)-6-METHYLPYRIMIDINE - A POTENTIAL SYNTHON FOR 5-(1-ORTHO-CARBORANYLMETHYL)PYRIMIDINES

被引：23

作者：

REYNOLDS, RC ^{[1
]}

TRASK, TW ^{[1
]}

SEDWICK, WD ^{[1
]}

机构：

[1] DUKE UNIV,DEPT MED,DURHAM,NC 27710

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 07期

关键词：

D O I：

10.1021/jo00007a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 with 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.

引用

页码：2391 / 2395

页数：5

共 28 条

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