1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54545751, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5-iodo-pyrimidin-4-yl)carbamic acid tert-butyl ester (1.46 g, 4.55 mmol) (reference example 44a) in DMF (15 mL) is added 4-ethynyl-benzoic acid methyl ester (0.721 g, 4.5 mmol)(reference example 46), copper iodide 99.999% (21 mg, 0.112 mmol), bis(triphenylphosphine)palladium(II)chloride (158 mg, 0.225 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.5 mL, 10 mmol). The resulting solution is heated to 100° C. and stirred for 1 hour then cooled to 20° C. The solution is diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 50% ethyl acetate, 5% methanol in hexanes) to give 601 mg of title compound as a yellow crystalline solid. 1H NMR (DMSO) δ 3.89 (s, 3H), 7.24 (s, 1H), 8.06 (d, J=8 Hz, 2H), 8.14 (d, J=8 Hz, 2H), 8.81 (bs, 1H), 9.05 (bs, 1H), 12.79 (bs, 1H). MS (ion spray) m/z 254 (M+H)+.

Provenance & Evidence