ALKYLATION OF 2-METHYLTHIO-4-HYDROXYPYRIMIDINES BY METHYL BROMOACETATE
2-Methylthio-4-hydroxypyrimidines react with methylbromoacetate in methanol-sodium methoxide solution to give O- and N(3)-alkylated products, namely, 2-methylthio-4-(methoxycarbonyl)methoxypyrimidines and 2-methylthio-3-(methoxycarbonyl)methylpyrimid-4-ones.
SYNTHESIS OF REGIOSPECIFICALLY SUBSTITUTED PYRIMIDYL DERIVATIVES AND THEIR INCORPORATION INTO PENEMS
Syntheses of regiospecifically substituted pyrimidines are described.Depending on the reaction conditions, N1- or N3-substituted pyrimidines are obtained.It has been shown that substitution on uracil under Mitsunobu conditions yields N1-substituted products.Incorporation of these derivatives into the penem nucleus gives penem antibiotics with extremely long half-lives.
Capraro, Hans-Georg,Lang, Marc,Schneider, Peter
p. 643 - 652
(2007/10/02)
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