TY - JOUR
T1 - 2,4-Dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine
T2 - A Potential Synthon for 5-(1-o-Carboranylmethyl)pyrimidines
AU - Reynolds, Robert C.
AU - Trask, Todd
AU - Sedwick, W. David
PY - 1991/3/1
Y1 - 1991/3/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0025765516&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0025765516&partnerID=8YFLogxK
U2 - 10.1021/jo00007a026
DO - 10.1021/jo00007a026
M3 - Article
AN - SCOPUS:0025765516
SN - 0022-3263
VL - 56
SP - 2391
EP - 2395
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -