Diethyl Ether → Methyl alpha-[4-methyl-6-(3-phenylphenoxy)-5-pyrimidinyl]-beta-dimethylaminoacrylate

Participants

Reaction Steps

Methyl [6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate (60 g, 0.18 mol) is added in one portion to a solution of t-BuOK (60 g, 0.53 mol) in 1,2-dimethoxyethane (0.51) at -40° C. After 1 hour dimethylformamide-dimethyl sulfate (1:1 adduct, 120 ml) is added at -50° C. The reaction mixture is allowed to warm to room temperature to give a yellow suspension. Addition of ether, washing repeatedly with brine and drying gives the crude methyl α-[4-methyl-6-(3-phenylphenoxy)-5-pyrimidinyl]-β-dimethylaminoacrylate (67 g, 95%) as an oil.

Provenance & Evidence