Guanidine Hydrochloride → 5-(naphthalen-2-ylmethyl)pyrimidine-2,4-diamine

Participants

Reaction Steps

2-(2-Naphthylmethyl)-3-anilinoacrylonitrile (6.65 g, 23.4 mmol) was dissolved in absolute ethanol (225 ml) and heated to reflux. A solution of sodium methylate (4.27 g, 79 mmol) in ethanol (75 ml) was mixed with guanidine hydrochloride (6.87 g, 72 mmol), filtered from salt, and added to the solution of 2-(2-naphthylmethyl)-3-anilinoacrylonitrile. The mixture was then refluxed for 8 hours, and allowed to stand at room temperature overnight. A yellow precipitate formed, which was isolated (2.66 g). An additional 1.33 g was obtained by concentration of the mother liquor. The combined fractions were recrystallized from absolute ethanol, yielding light cream colored 2,4-diamino-5-(2-naphthylmethyl)pyrimidine (3.0 g), m.p. 231°-233° C. Anal. Calcd. for C15H14N4 : C, 71.98; H, 5.64; N, 22.38. Found: C, 71.93; H, 5.68; N, 22.35.

Provenance & Evidence