Imidazole → HCID 21243175, compound

Participants

Reaction Conditions

Reaction Steps

6.21 g (9.1 mmol) of 2-bromomethyl-2-(2,4-dichlorophenyl)-4-[4-(4-(2-methyl-4-(4-tolyl)pyrimidin-6-yl)piperazin-1-yl)phenoxymethyl]-1,3-dioxolane (mixture of cis/trans diastereomers) were reacted with 1.244 g (18.3 mmol) of imidazole and 0.55 g (18.2 mmol) of an 80% strength sodium hydride/oil dispersion in 26 ml of absolute dimethyl sulfoxide as described in Example 8b. After stirring for 26 hours at 130° C., the dimethyl sulfoxide (DMSO) was removed by distillation in an oil-pump vacuum. The residue remaining was taken up in CH2Cl2 /water. After thorough mixing and subsequent separation of the phases, the aqueous solution was extracted three times with CH2Cl2. The combined CH2Cl2 extracts were evaporated in vacuo. The residue remaining (4.30 g) was chromatographed on a silica gel S/CH2Cl2 column (diamter 2.0 cm, height 20 cm) with elution using CH2Cl2 and CH2Cl2 /C2H5OH mixtures (0.5-3.0% by volume of C2H5OH). The fractions containing the diastereomer racemates (check using TLC) were combined and evaporated in vacuo. In this fashion, 3.12 g (=51% yield) of 2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-4-[4-(4-(2-methyl-4-(4-tolyl)pyrimidin-6-yl)piperazin-1-yl)phenoxymethyl]-1,3-dioxolane (mixture of cis/trans diastereomers) were obtained as a viscous oil;

Provenance & Evidence