GB1291417A - Nitrofuryl-triazole-pyrimidines - Google Patents

Abstract

1291417 Nitrofuran derivatives BOEHRINGER MANNHEIM GmbH 19 April 1971 [3 Feb 1970] 20778/71 Heading C2C Novel compounds of Formula I (in which TP represents a triazolo-pyrimidine ring system, and each of R 1 , R 2 and R 3 is H, halogen, OH, NH 2 , alkyl, alkoxy, acyloxy, alkylamino, acylamino or haloacylamino) are prepared by (a) nitration of compounds of Formula II or (b) oxidative cyclization of hydrazones of Formulµ III and III<SP>1</SP> (in which Py, together with the -N = C< group, forms a pyrimidine ring) or (c) cyclization of hydrazides of Formulµ IV and IV<SP>1</SP> with the splitting off of water, or (d) condensation of aminotriazoles of Formula V (in which R 4 has the same meaning as R 1 or represents a 5-nitro-2-furyl group) with a 1,3- dicarbonyl compound of the formula (in which R 4 has the above given meaning but with the proviso that only one of the symbols R 4 represents a nitrofuryl group, or with a derivative of such a 1,3-dicarbonyl compound in which one of the -COR 4 groups is replaced by a nitrile group) or (e) cyclization of diaminopyrimidines of Formula VI with nitrous acid. In a resulting compound I the substituents R 1 , R 2 and R 3 may be converted into one another in known manner. The nitrofuryl-s-triazolo-[2,3-a]-pyrimidines may be prepared by rearrangement of the corresponding s-triazolo-[4,3-a]-pyrimidines. Compounds of Formula III<SP>1</SP> are prepared by reaction of 5-nitro-2-furan-aldehyde with appropriate hydrazino-pyrimidines, which are themselves prepared by reaction of the corresponding chloro-pyrimidines with hydrazine. Compounds of Formula II are prepared by cyclization of appropriate furyl-hydrazino-pyrimidines (themselves prepared by reaction of (chloro or alkylthio)-furyl-pyrimidines with hydrazine. 1H - 5 - (2 - furyl) - 7 - hydroxy - vtriazolo-[4,5-d]-pyrimidine is prepared by reaction of 2-(2-furyl)-4,5-diamino-6-hydroxypyrimidine with nitrous acid. 4 - (5 - Nitro - 2 - furyl) - 6 - hydrazino - pyrimidine is prepared by desulphurizing 2-mercapto - 4 - (2 - furyl) - 6 hydroxy - pyrimidine with Raney nickel to form 4-(2-furyl)-6-hydroxypyrimidine, reacting this with POCl 3 to form the chloro compound and treating this with hydrazine hydrate. 2 - Amino - 4 - (2 furyl) - 5 - methyl - 6 - chloropyrimidine is prepared by reacting 2-acetamido- 4 - (2 - furyl) - 5 - methyl - 6(1H) - pyrimidinone with thionyl chloride. Antibacterial compositions for oral or parenteral administration comprise a compound of Formula I together with a pharmaceutical carrier.