Potassium Carbonate → 6-Methyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-amino-6-methyl-pyrazine-2-carboxylic acid ethyl ester (500 mg, 2.8 mmol), 5-bromopyrimidine (614 mg, 3.9 mmol), water (104 μl, 5.8 mmol) and potassium carbonate (686 mg, 5.0 mmol) in xylene (7 ml) was vented with argon. Palladium(II) acetate (25 mg, 0.11 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 80 mg, 0.14 mmol) were consecutively added under inert gas atmosphere and the reaction mixture was heated to 140° C. and stirred for 5 h. After cooling-down to ambient temperature, the reaction mixture was diluted with water (5 ml) and extracted with methylenechloride. The organic layers were washed with water and brine, dried and concentrated in vacuo. The product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (585 mg, 81.8%). MS: M=260.1 (M+H)+

Provenance & Evidence