Cesium carbonate → HCID 57731560, compound

Participants

Reaction Conditions

Reaction Steps

A vial is charged with 120 mg (0.49 mmol) of 2-amino-5-bromo-N,N-dimethyl-benzamide, 11.4 mg (12 μmol) of tris(dibenzylideneacetone)dipalladium(0), 15.9 mg (27 μmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (XantPhos), 290 mg (0.89 mmol) of cesium carbonate, and 159 mg (1.00 mmol) of 5-bromo-pyrimidine. The vial is flushed with nitrogen and 2 mL of anhydrous 1,4-dioxane are added. The vial is sealed and heated to 100° C. for 17 h. The resulting mixture is diluted with methanol and dichloromethane and filtered over a 0.45 μm PTFE syringe filter. The filtrate is evaporated and the residue purified by flash chromatography on silica gel using a gradient of ethyl acetate containing 10% v/v of methanol in hexanes to afford 115.6 mg (0.39 mmol, 80%) of 5-bromo-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide as an ivory solid. 1H-NMR (500 MHz, d6-DMSO): δ 8.66 (s, 1H), 8.48 (s, 2H), 8.13 (s, br., 1H), 7.51 (dd, 1H), 7.43 (d, 1H), 7.23 (d, 1H), 2.86 (s, 3H), 2.81 (s, 3H); MS: m/z 321.0+323.0 (M+H+).

Provenance & Evidence