2,6-Dimethoxybenzoic Acid → 5-(4-Amino-3,5-dimethoxybenzyl)-2,4-(1H,3H)-pyrimidinedione

Participants

Reaction Steps

A mixture of 10.04 g (49 mmol) of 5-[(dimethylamino)methyl]uracil hydrochloride (B. Roth, J. Z. Strelitz, and B. S. Rauckman, J. Med. Chem. 23, 379 (1980) and 7.48 g (49 mmol) of 2,6-dimethoxyaniline (m.p. 73°-74.5°; prepared from 2,6-dimethoxybenzoic acid by the procedure in Org. Reactions 3, 330 (1946)) in 50 mL of ethylene glycol under nitrogen was heated at 145° for 5 hours. The mixture was cooled and the precipitated solid was collected, suspended in 300 mL of boiling ethanol and collected to give 3.91 g (29%) of the title compound; m.p. 243°-245° (dec.).

Provenance & Evidence