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New pyrimidino‐crown ether ligands
Author(s) -
Redd J. Ty,
Bradshaw Jerald S.,
Huszthy Peter,
Izatt Reed M.
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310459
Subject(s) - chemistry , derivative (finance) , methanol , crown ether , pyrimidine , diamine , hydrochloride , ether , organic chemistry , medicinal chemistry , stereochemistry , ion , financial economics , economics
Eight new macrocyclic ligands containing the pyrimidine subcyclic unit ( 3‐10 , Figure 1) have been prepared. Two of these new crown ethers are chiral. Pyrimidino‐crowns 3‐8 were prepared by treating the di‐tosylate derivative of the appropriate oligoethylene glycol with 4‐methoxy‐5‐raethyl‐2,6‐pyrimidinedimeth‐anol in basic conditions. The yields were in the 30‐50% range giving the crowns as viscous oils. Chiral dimethyl‐substituted pyrimidino‐crown 9 was prepared from 4‐methoxy‐5‐methyl‐2,6‐pyrimidinedimethyl di‐tosylate and chiral dimethyl‐substituted tetraethylene glycol. Treatment of dimethyl 4‐methoxy‐5‐methyl‐2,6‐pyrimidinedicarboxylate with the diamine derivative of chiral dibenzyl‐substituted tetraethylene glycol gave the chiral dibenzyl‐substituted pyrimidino‐crown diamide 10. Starting 4‐methoxy‐5‐methyl‐2,6‐pyrimidinedi‐methanol was prepared by a six step process from acetamidine hydrochloride and diethyl oxalpropionate.