Triaminopyrimidine derivative

Fig. 1.3. Cyclic and polymeric supramolecular aggregates formed by hydrogen-bond self-assembly of barbituric acid and 2,4,6-triaminopyrimidine derivatives.

Triaminopyrimidine and barbituric acid derivatives are complementary components presenting the required features, since they should be able to form two arrays of three hydrogen bonds with each other. However, as pointed out above, based solely on hydrogen bonding recognition, their association could yield either a linear or a macrocyclic supramolecular structure (Section 9.4.2 Figure 37). 

Replacement of the benzene ring with heterocycles was also investigated (Table 3.3). Condensation of a suitably substituted heterocyclic amine with (464), followed by imine reduction and saponification, afforded (583)-(588) (Scheme 3.121) [243-246], Thiophene derivative (589) was prepared by the condensation of 6-hydroxy-2,4,5-triaminopyrimidine, 1,1,2-trichloroacetone and A-(5-aminothienyl)-L-glutamic acid [247]. The pyridine analogue of AP,... 

The sulphonyl derivatives of FA and AP, (608) and (610), respectively, were also prepared. Thus, condensation of 6-hydroxy-2,4,5-triaminopyrimidine with sulphonyl glutamate (607) afforded (608) (Scheme 3.130) [256], AP congener (610) was synthesized by alkylation of the requisite elaborated aniline (609) with (26) HBr (Scheme 3.131) [73, 248]. 

Reaction of ethyl a-(arylmethyl)acetoacetate with 2,4,6-triaminopyrimidine gave 7-pyrido[2,3-rf]pyrimidinones <85USP4512992,88EUP279565). Reactions of glycopyranosylaminopyrimidinones with malonic acids in Ac20 afforded the derivatives (343) <91M255>. 

An unusual formyl ketone equivalent which has been used for the synthesis of biopterin (10, X = H) via the actyl derivative 10 (X = Ac) is the phenylhydrazone of 5-deoxy-L-ribose (9) which has been condensed with 2,5,6-triaminopyrimidin-4(3/7)-one.78... 

Pyrimidines bearing amino groups adjacent to a carboxylic acid152,203,204 or carboxylic acid derivatives 1 10,205 208 have been used in the synthesis of pyrimido[5,4-r/]pyrimidines. Thus, methyl 2,5,6-triaminopyrimidine-4-carboxylate (1) on heating with benzamidine at 100 C furnishes 6,8-diamino-2-phenylpyrimido[5,4- f]pyrimidin-4-ol (2).110... 

The 5-amino derivative of cytosine is reported to inhibit riboflavin synthesis [399]. 4,5,6-Triaminopyrimidine inhibits both synthesis and growth by 60 per cent. 4,5,6-Triamino-2-hydroxypyrimidine inhibits synthesis, but not growth, of riboflavin [400]. 

Fig. 4 Two-component (left) and single-component (right) ID self-assembly. Barbituric acid (10a) and triaminopyrimidine (10b) derivatives self-assemble through complementary hydrogen bonds into linear tapes (left)." " At the right, the crystal packing of his-urea compound PI is shown, in which the urea groups form a ID (a-network) hydrogen-bonded array. (From Ref. [29].) View this art in color at www.dekker.com.)...

Huge success of benzodiazepenes as pharmaceutical scaffolds has prompted preparation and evaluation of het-erocyde-annulated benzodiazepine derivatives. A tandem Michael addition-condensation sequence xmder MW irradiation was also proved to be useful for the synthesis of amino-substituted pyrimidine-fused diazepine derivatives of the type 96 from 4,5,6-triaminopyrimidine and chalcones [57]. Similarly, the pyridine-fused derivatives (97) were prepared xmder MW-assisted solvent and catalyst-free condition [58], Condensation of thiadiazole-annulated phen-ylene diamines with appropriate carbonyl compounds using sulfamic acid as organocatalyst led to the formation of corresponding diazepine derivatives 98 in excellent yields [59] (Figure 4). 

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