N-[4-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide → 4-amino-N-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-yl)-benzenesulfonamide
Reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:6]=[C:5]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24]C(=O)C)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:4]=1>[OH-].[Na+]>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([NH:14][C:5]2[CH:4]=[C:3]([NH:2][CH3:1])[N:8]=[C:7]([N:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[N:6]=2)(=[O:16])=[O:17])=[CH:19][CH:20]=1Participants
3
Procedure
0.30 g (0.00077 mol) of N-[4-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide was boiled at reflux in 30 ml of 1N aqueous sodium hydroxide for 3 hours. The mixture was cooled and extracted with ethyl acetate. Crystals then separated from the aqueous phase and, after suction filtration, were chromatographed over silica gel with ethyl acetate/ethanol 9:1 as the eluent. There was obtained 0.082 g (30%) of 4-amino-N-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-yl)-benzenesulfonamide as beige crystals; m.p. 299-301° C.