Hydrochloric Acid → HCID 86699278, compound

Participants

Reaction Conditions

Reaction Steps

643 mg of cyclopropylboronic acid, 680 g of copper(II) acetate, 1.37 g of dimethylaminopyridine and, finally, 6.23 ml of a solution of sodium bis(trimethylsilyl)amide (0.6M in toluene) are added, using a dropping funnel, to a solution of 1 g of ethyl [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, prepared in step 1d of example 1d, in 12 ml of toluene. The reaction mixture is heated at 95° C. for 16 and then cooled to ambient temperature. After the addition of 20 ml of an aqueous 1N hydrochloric acid solution and extraction with dichloromethane (3×50 ml), the organic phases are combined and then dried over magnesium sulfate, filtered through sintered glass, and concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of dichloromethane and methanol (98/02 then 95/05 V/V). 90 mg of ethyl (1-cyclopropyl-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate are obtained in the form of a yellow oil, used as it is in the next step.

Provenance & Evidence