Aniline → Pyrimido(5,4-d)pyrimidine

Participants

Reaction Steps

In accord with the synthesis illustrated above, 4 g (19 mmol) of 2,4,6,8-tetrachloropyrimidopyrimidine was added to 50 ml of chloroform, and 8.7 ml (95 mmol) of aniline was slowly added in droplets thereto in a bath at 0° C. After the completion of the reaction was confirmed through TLC, the resulting reaction solution was washed with an aqueous ammonium chloride solution and then extracted with chloroform to separate an organic layer. Thereafter, the organic layer was distilled under reduced pressure to remove the solvent and then dried in an oven, yielding 5 g of a pale yellow solid 5a NMR analysis of the pale yellow solid produced the following data: 1H-NMR (DMSO-d6) d(ppm) 7.23 (t, 2H, J=7.3 z), 7.46 (t, 41, J=7.8 Hz), 7.87 (t, 4H, J=8.1 Hz), 8.66 (s, 2H).

Provenance & Evidence