4,5-Diaminopyrimidine → HCID 178424861, compound

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([N:27]=[C:28]=S)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:40][C:41]1[C:46]([NH2:47])=[CH:45][N:44]=[CH:43][N:42]=1>[Hg]=O>[NH3:8].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([NH:27][C:28]3[NH:40][C:41]4[C:46]([N:47]=3)=[CH:45][N:44]=[CH:43][N:42]=4)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Procedure

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-isothiocyanato-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (210 mg in 5 mL toluene) was added 250 mg mercury(II) oxide followed by 130 mg 4,5-diaminopyrimidine and the mixture heated to reflux on an oil bath. After 48 hours, the mixture was cooled to room temperature and the reaction quenched by the addition of 2N hydrochloric acid (4 mL). The solvents were removed in vacuo and the residue treated with 2N ammonia in methanol (10 mL) then concentrated once again. The residue was washed with chloroform and the solids removed by filtration. Concentration of the organics and purification by flash chromatography on silica gel (ethyl acetate:hexane, 1:1; then chloroform:2N ammonia in methanol, 9:1) gave the title compound (10 mg).