Acetic Acid → HCID 11538495, compound

Participants

Reaction Steps

A mixture of 370 mg (0.968 mmol) of N-[6-(2-hydroxy-ethylamino)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide, 0.074 ml (0.912 mmol) of formaldehyde solution (37% in water), 4 ml of acetic acid, 15 ml of tetrahydrofuran and 15 ml of water is hydrogenated in presence of 115 mg of palladium on carbon for 3 days. After day 1 and 2 another portion of formaldehyde (0.074 ml) is added. After filtration of the reaction mixture the tetrahydrofuran is evaporated and the remaining aqueous phase extracted with ethyl acetate. The organic phase is washed with brine, dried over Na2SO4 and concentrated to dryness leaving a brown oil that is fractionated by medium pressure chromatography on a RP-18 column (20 μm particle size) with acetonitril/water 1:2. The fractions containing the product are combined and extracted with ethyl acetate, the organic phase dried over Na2SO4 and concentrated yielding 165 mg of N-{6-[(2-hydroxy-ethyl)-methyl-amino]-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl}-methanesulfonamide as yellow powder, m.p. 220-224° C.

Provenance & Evidence