Toluene → 3-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-[6-(3-dimethylaminomethyl-phenylamino)-pyrimidin-4-yl]-1-ethyl-urea

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Reaction Steps

A suspension of 2,6-dichloro-3-methoxyphenylisocyanate (2 eq.) in toluene (3 ml) is added to a refluxing solution of N-(3-dimethylaminomethyl-phenyl)-N′-methyl-pyrimidine-4,6-diamine (216 mg, 0.80 mmol, 1 eq.) in toluene (3 ml), under an argon atmosphere. The resulting mixture is stirred at reflux for 2 h and allowed to cool to RT. The reaction mixture is diluted with EE and a saturated aqueous solution of sodium bicarbonate. The aqueous layer is separated and extracted with EE. The organic phase is washed with brine, dried (sodium sulfate), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5), followed by reversed phase MPLC purification (AcCN/H2O/TFA) of the resulting product, affords 161 mg of the title compound as a white solid: ESI-MS: 518.9/520.9 [MH]+; tR=3.76 min (purity: 100%, gradient J); TLC: Rf=0.21 (DCM/MeOH+1% NH3aq, 95:5).

Provenance & Evidence