2,4,6-trichloropyrimidine. Reaction with ethanolamine and diethanolamine

2,4,6-Trichloropyrimidine, 1, reacts with neutral nucleophiles, such as ethanolamine and diethanolamine, to produce both mono- and disubstituted derivatives resulting from replacement of either one (2 and 3) or two (4) chlorine atoms. The third chlorine could not be replaced by these nucleophiles. Failure of this final step was attributed to intramolecular hydrogen bonding of the nucleophiles.