3-Chloroaniline → HCID 23282755, compound

Participants

Reaction Steps

With the exclusion of air, 529 μl (5.0 mmol) of 3-chloro-aniline are added to approximately 1.2 mmol of 4-chloro-5-methyl-6-(N-benzyl-pyridinium-2-yl)-7H-pyrrolo[2,3-d]-pyrimidine in 10 ml of isopropanol and the reaction mixture is boiled under reflux for 3 hours. The reaction mixture is concentrated by evaporation and the residue is chromatographed over silica gel. Elution with methylene chloride/ethanol (7:3) and methylene chloride/methanol (7:3) yields first 4-(3-chloro-anilino)-5-methyl-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (A) and then 4-(3-chloro-anilino)-5-methyl-6-(N-benzyl-pyridinium-2-yl)-7H-pyrrolo[2,3-d]pyrimidine bromide (B). A is also obtained by heating B. A: m.p. 251-252° C.; 1H-NMR (200 MHz, DMSO-d6): 12.75 and 9.25 (2sb), 8.75 (d, J=5, 1H), 8.35 (s, 1H), 8.05-7.85 (m, 3H), 7.66 (d, J=8, 1H), 7.45 (m, 2H), 7.29 (d, J=8, 1H), 2.84 (s, 3H); FAB-MS: (M+H)+ =336. B: m.p. 171-172° C. (intense foaming); 1H-NMR (200 MHz, DMSO-d6): 12.65 (sb), 9.48 (d, J=6, 1H), 8.80 (t, J=8, 1H), 8.59 (sb, 1H), 8.43 (s, 1H), 8.3 (m, 2H), 7.94 (m, 1H), 7.72 (d, J=8, 1H), 7.40 (t, J=8, 1H), 7.28 (m, 3H), 7.17 (d, J=8, 1H), 6.94 (m, 2H), 5.93 (s, 2H), 2.27 (s, 3H); FAB-MS: (M+H)+ =426.

Provenance & Evidence