Trimethylamine → 4-(4-Amino-naphthalen-1-yloxy)-pyrimidine-2-carbonitrile

Participants

Reaction Steps

To a 0° C. solution of trimethyl amine (20% solution in water, 3.8 mmol) in 2 mL of dimethylformamide was added 4-(2-chloro-pyrimidin-4-yloxy)-naphthalen-1-ylamine (270 mg, 1 mmol). The deep tan solution was warmed to room temperature for 3 h, during which the initially light suspension became a brown suspension. After this time, tetraethylammonium cyanide (156 mg, 1 mmol) was added all at once to provide a deep amber solution. After 1 h, the reaction was quenched with water, extracted with EtOAc and dried over magnesium sulfate. Column chromatography (10-60% EtOAc-hexanes) provided 142 mg (54%) of 4-(4-amino-naphthalen-1-yloxy)-pyrimidine-2-carbonitrile.

Provenance & Evidence