Ammonium Hydroxide → 5-[4-(2,6-Dimethyl-pyridin-4-yl)-3,5-diethoxy-benzyl]-pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

5-(3,5-Diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamine (example 1) (414 mg; 1 mmol), 2,6-dimethyl-4-trimethyltin-pyridine (404 mg; 1.5 mmol), bis(triphenyl-phosphine)palladium dichloride (20 mg) and a few crystals of 2,6-di-tert-butyl-4-methylphenol are dissolved in dimethylformamide (5 ml) and the solution is stirred for 24 hours at 140° C. while gassing with argon. The reaction mixture is concentrated, a little water is added to the residue obtained, the pH is adjusted to 8 by addition of NH4OH conc. and the entire mixture is filtered with suction. The mother liquor is concentrated and the residue is chromatographed over silica gel (30 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05). 26 mg (6.6%) 5-[4-(2,6-dimethyl-pyridin-4-yl)-3,5-diethoxy-benzyl]-pyrimidine-2,4-diamine are obtained as a yellow powder.

Provenance & Evidence