Hydrochloric Acid → HCID 178450868, compound

Participants

Reaction Conditions

Reaction Steps

2-(2-Bromophenyl)acetimidamide hydrochloride (2 g, 8.01 mmol, Eq: 1.00) and 4-tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarate (4) (3.44 g, 11.2 mmol, Eq: 1.39) were dissolved in methanol (40.0 ml) and cooled down to 0° C. At that temperature sodium methoxide (1.37 g, 24.0 mmol, Eq: 3) was added. After another 15 minutes at this temperature, the resulting suspension was allowed to warm to room temperature overnight. A little methanol (˜5 ml) was added and the yellow suspension was cooled to 0° C. 1M HCl (˜50 ml) was added and a precipitate formed. The suspension was stirred for −20 minutes. The solid was collected by filtration, washed with water and a little methanol/water 9/1 and dried to afford 5-(benzyloxy)-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid tert-butyl ester (2.69 g, 5.71 mmol, 71.2% yield) (67) as an off-white solid.

Provenance & Evidence