4-chloro-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine → 4-(3-Chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
Reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=CC=C[N:12]=3)NC=2N=CN=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[NH:32][C:26]2[N:27]=[CH:28][N:29]=[C:30](O)[C:25]=2[CH:24]=1>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:16]=[C:11]([CH:9]=[CH:10][CH:3]=1)[NH:12][C:30]1[C:25]2[CH:24]=[C:23]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=3)[NH:32][C:26]=2[N:27]=[CH:28][N:29]=1Participants
4
Procedure
4-Chloro-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine With the exclusion of moisture, 7.05 g (33.2 mmol) of 6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]-pyrimidin-4-ol and 70 ml of phosphorus oxychloride are heated at boiling for 2 hours. The dark-brown suspension is concentrated by evaporation to a residual volume of 20 ml. The residue is introduced in portions into water, neutralized with solid NaHCO3 and 0.2 liter of ethyl acetate is added thereto. Filtering and washing with hot THF yield the title compound; 1H-NMR (300 MHz, DMSO-d6): 13.2 (sb, 1H), 8.72 (d, J=7, 1H), 8.63 (s, 1H), 8.23 (d, J=11, 1H), 7.97 (t, J=11, 1H), 7.46 (dd, J,=7, J2 =11, 1H), 7.35 (s, 1H). Further product can be isolated from the filtrate and the THF washing solution, which is concentrated by evaporation, by partitioning between ethyl acetate/water and digesting in ethyl acetate/diethyl ether.