1-Naphthalenemethanol → 6-Chloro-2-(1-naphthylmethoxy)pyrimidin-4-amine

Participants

Reaction Steps

1-Naphthalenemethanol (227 mg, 1.44 mmol) is added to a slurry of 50% sodium hydride (69 mg, 1.44 mmol) in dry THF (4 ml) at 0° C. After stirring for 30 minutes, 4-amino-2,6-dichloropyrimidine (157 mg, 0.96 mmol) is added and stirred at 22° C. for 72 hours. The solution is quenched with saturated NH4Cl and concentrated in vacuo. The residue is dissolved in methylene chloride and washed 3× saturated NaHCO3, dried with MgSO4, filtered, and concentrated in vacuo. The sample is purified by chromatography using 1:2 ethyl acetate/hexanes and recrystallization from heptane/toluene, mp 160-161° C.

Provenance & Evidence