Bromoacetyl bromide → HCID 135738551, compound

Participants

Reaction Steps

Aluminum trichloride (1.34 g, 0.010 mol) was added portionwise to a stirred solution of 6-(2-ethoxyphenyl)-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (Example 13; 1.0 g, 0.0034 mol) and bromoacetyl bromide (1.35, 0.0067 mol) in dichloromethane (30 ml) at 0° C. The reaction solution was allowed to warm to room temperature, stirred for 14 hours, then for a further 2 hours under reflux. The cool reaction mixture was added dropwise to ice/water (50 g) and the resulting mixture stirred for 1 hour. The organic phase was separated and the aqueous phase extracted with dichloromethane (2×50 ml); the combined organic solutions were then washed with brine (10 ml) and dried (Na2SO4). Removal of the solvent by evaporation under vacuum gave an off-white solid which, when triturated with ether (20 ml) and dried, afforded the product as a white solid (1.29 g, 92%). A sample crystallised from ethyl acetate-hexane as colourless crystals, m.p. 164-166° C. Found: C, 51.88; H, 4.56; N, 13.13. C18H19BrN4O3 requires C, 51.56; H, 4.57; N, 13.36%.

Provenance & Evidence