Tetrahydrofuran → HCID 11574784, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1 g (1.96 mmol) of N-{6-[4-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-methanesulfonamide, 0.738 g (2.34 mmol) of tetrabutylammonium fluoride trihydrate and 20 ml of tetrahydrofuran is stirred at 50° C. for 18 hours. The reaction mixture is concentrated to dryness and the residue fractionated by medium pressure chromatography on a RP-C18 column (20 μM material) with acetonitril/water 1:1 (containing 0.1% trifluoroacetic acid) as eluent. The residue obtained by evaporation of fractions 2-5 is dissolved in water and the pH adjusted to ˜5 with diluted NH4OH solution. The product precipitates and is collected by filtration. The residue obtained from fractions 6-13 is fractionated by medium pressure chromatography on a RP-C18 column (20 μM material) with acetonitril/water 1:2 as eluent. During concentration of the fractions the product precipitates and is collected by filtration. Crystallization of all combined product fractions from DMSO/water gives 0.328 g of N-[6-(4-hydroxymethyl-imidazol-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide as a yellow powder, m.p. >300° C.

Provenance & Evidence