Hydrochloric Acid → 5-(7-Allyl-8-hydroxy-5-quinolylmethyl)-2,4-diaminopyrimidine

Participants

Reaction Steps

7-Allyl-8-hydroxyquinoline [H. Fiedler, Arc. Pharm., 297, 108 (1964)] (33.0 g, 0.227 mol), 2,4-diamino-5-hydroxymethylpyrimidine (32.97 g, 0.227 mole), glacial acetic acid (300 mL) and concentrated HCl (31.5 mL) were refluxed for 5 hr. The resulting precipitate was filtered off and then slurried with H2O (250 mL) and sufficient NH4OH to give a pH of 8. The undissolved solid was filtered off, washed with H2O and dried to give the title compound as yellow powder (19.7 g, 28%), mp 229°-231° dec., structure confirmed by NMR. Anal. Calcd for C17H17N5O: C, 66.43; H, 5.58; N, 22.79. Found: C, 66.41; H, 5.59; N, 22.78. Additional product (5.0 g, 7%) was obtained by evaporation of filtrates and chromatography to separate unreacted starting materials.

Provenance & Evidence