7-Amino-5-[(4-benzyloxyphenyl)methyl]amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine → HCID 16128681, compound

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Reaction Steps

A solution of 7-amino-5-[(4-benzyloxyphenyl)methyl]amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine (2.37 g) in ethyl acetate (150 ml) and methanol (150 ml) was treated with 10% palladium on carbon (3.0 g) and hydrogenated at atmospheric pressure for 2.5 hours. The catalyst was filtered through diatomaceous earth and the liquors evaporated. The residue was purified by chromatography on silica (100 g) eluting with dichloromethane containing methanol 3-30% v/v, and gave 7-amino-2-(2-furyl)-5-[(4-hydroxyphenyl)methyl]amino-[1,2,4]-triazolo[1,5-a][1,3,5]triazine, m.p. 268-270; NMR: 4.39 (d, 2H, CH2N), 6.64 (d of d, 1H, furyl-4H), 6.68 and 7.13 (A2B2 pattern, 4H, phenyl-H), 7.03 (d, 1H, furyl-3H), 7.8 (t, 1H, NH), 7.84 (d, 1H, furyl-5H), 8.13 (br s, 2H, NH2) and 9.19 (s, 1H, OH); m/e 324 (M+H)+.

Provenance & Evidence