6-(Pyrimidin-5-YL)hexan-1-amine → (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-N-[6-(5-pyrimidinyl)hexyl]-2-propenamide

Participants

Reaction Steps

As in Example 114, (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl ester (1.21 g) was reacted with 5-pyrimidinehexanamine (0.505 g) in tetrahydrofuran (20 mL) at room temperature overnight and then at 50° C. for 1.5 hour. The product was isolated in the usual manner then was purified by HPLC (ethyl acetate) and twice crystallized from ethyl acetate-hexane to provide 0.86 g of (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-N-[6-(5-pyrimidinyl)hexyl]-2-propenamide, mp 128°-129° C. Anal. Calcd for C28H35N3O2 : C, 75.47; H, 7.92; N, 9.43 Found: C, 75.52; H, 7.95; N, 9.40

Provenance & Evidence