2-Bromopyrimidine → N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine (112 mg) in dioxane (1.45 ml) was added 2-bromo-pyrimidine (69 mg, 1.5 eq.), 1,3 Bis(2,6-di-i-propylphenyl)imidazolium chloride (20 mg, 0.16 eq.), Tris(dibenzylideneacetone)dipalladium (21 mg, 0.8 eq.) and potassium t-butoxide (49 mg, 1.5 eq.). The reaction mixture was heated at 100° C. for 16 h, poured into saturated sodium bicarbonate (50 ml), extracted 2×50 ml of CH2Cl2, dried MgSO4, filtered and concentrated. Purification via MPLC chromatography eluting with 20–50% ethyl acetate/heptane provided the title compound as an amorphous solid (70 mg, 52%):

Provenance & Evidence