3-Chloroaniline → 4-(3-Chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, 40 ml of DMPU are added to 6.53 g (28.3 mmol) of 4-chloro-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine and 4.46 ml (42.5 mmol) of 3-chloro-aniline in 90 ml of n-butanol and the reaction mixture is stirred at 140° C. for 12 hours. The dark-brown suspension is cooled and filtered. Further product can be obtained from the mother liquor by precipitation with 100 ml of water. Digestion with ethanol/THF yields the title compound; m.p.>300° C.; 1H-NMR (360 MHz, DMSO-d6): 12.49 and 9.66 (2s, 2H), 8.63 (d, J=5, 1H), 8.40 and 8.25 (2s, 2H), 7.91 (m, 2H), 7.84 (d, J=8, 1H), 7.57 (s, 1H), 7.33 (m, 2H), 7.06 (d, J=8, 1H); HPLC: tRet (Grad20)=10.1 min; MS: (M)+ =321.

Provenance & Evidence