GB776267A - New substituted phenanthridine compounds - Google Patents

Abstract

The invention comprises phenanthridines of the general formula: <FORM:0776267/IV(b)/1> wherein R2, R3 and R4 represent alkyl groups which may be the same or different, R1 represents an alkyl, aralkyl or aryl group which may be unsubstituted or may carry on amino or nitro group as a substituent, and the preparation thereof by condensing a phenanthridine of the general formula: <FORM:0776267/IV(b)/2> wherein R1 and R2 have the above significance and Y represents an anion which may be identical with X, with a halopyrimidine of the general formula: <FORM:0776267/IV(b)/3> wherein A represents a halogen atom, R3 and R4 have the above significance, and Z is an anion which may be identical with X, and if Y and Z are not identical with X, the product is treated to replace Y and/or Z by X. In the case where R1 represents a nitroaryl group, the 9-nitroaryl substituted phenanthridine product of the above general formula may be reduced to form a 9-aminoaryl substituted phenanthridine product of the above general formula. The condensation may take place in an aqueous medium and the presence of an acid is advantageous to accelerate the reaction. In the examples: (1) 3 - (21 - amino - 61 - methylpyrimidyl - 41 - amino) - 9 - methylphenanthridine 10,11-eimethiodide is prepared by reacting 3-amino-9,10-dimethylphenanthridinium bromide and 2 - amino - 4 - chloro - 6-methylpyrimidine - methiodide and the reaction product is treated with potassium iodide in boiling water; by treatment with silver methane sulphonate the corresponding 10,11-dimethomethane sulphonate is obtained; (2) 3 - (21 - amino - 61 - methylpyrimidyl - 41-amino) - 9 - phenylphenanthridine 10,11 - -di methiodide and the dimethomethane sulphonate thereof are prepared as in (1); (3) 3-(21-amino-61 - methyl - pyrimidyl - 41 - amino) - 9 - p-nitrophenyl - phenanthridine 10 : 11 - dimethiodide is prepared by reacting 3-amino-10-methyl - 9 - p - nitrophenylphenanthridinium bromide and 2 - amino - 4 - chloro - 6 - methylpyrimidine 1-methiodide and the reaction product is heated with aqueous potassium iodide; this compound is converted into 3-(21-amino-61-methyl - pyrimidyl - 41 - amino) - 9 - p - aminophenylphenanthridine 10 : 11 - dimethiodide by reduction using a sludge prepared by mixing saturated solutions of ferrous sulphate and barium hydroxide, and by treatment with silver methane sulphonate the 10 : 11-dimethomethane sulphonate thereof is obtained.