2,4,6-Trichloropyrimidine → 2,6-Dichloro-N-propylpyrimidin-4-amine

Participants

Reaction Steps

A mixture of 2,4,6-trichloropyrimidine (I, 11 g) in THF (160 ml) is cooled to -70°. Diisopropylethylamine (11 ml) is added, followed by the addition of a mixture of n-propylamine (II, 4.9 ml) in THY (15 ml). The mixture is allowed to stand for 3 days at 20°-25° and then is concentrated. The residue is partitioned between ethyl acetate and aqueous potassium bicarbonate. The organic extract is washed with water and saline, then dried and concentrated to give a solid. The solid is chromatographed on silica gel (650 g) packed in ethyl acetate/hexane (10/90) and eluted with ethyl acetate/hexane (10→30/90→70). The appropriate fractions (14-18) are pooled and concentrated to give the tire compound, NMR (CDCl3) 6.29, 5.87, 3.21, 1.65 and 0.99δ.

Provenance & Evidence