(tert-Butyldimethylsilyloxy)methyl Chloride: Synthesis and Use as N-Protecting Group in Pyrimidinones.

Abstract

A new reagent, (tert-butyldimethylsilyloxy)methyl chloride (3) has been synthesized by sulfuryl chloride cleavage of (tert-butyldimethylsilyloxy)methyl ethyl sulfide (2). The latter was prepared from tert-butyldimethylsilyl chloride and ethylthiomethanol. The chloromethyl ether 3 has been used for the protection of the NH functionality in 5-halo-2(1H)-pyrimidinones and for the protection of the N-1 in N-3 alkylation of thymine.