3-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole → 6-{1-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1H-[1,2,3]triazol-4-ylmethoxy}-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazine

Participants

Reaction Steps

The reaction was carried out according to Example 1 step 4 using {1-[2-(tert-butyldimethylsilanyloxy)ethyl]-1H-[1,2,3]triazol-4-yl}methanol (1.67 g, 6.49 mmol) and 6-chloro-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (1.85 g, 6.49 mmol). The crude residue was purified by column chromatography on silica using 2-3% MeOH/CH2Cl2 containing 1% NH3 to yield the desired phthalazine (2.82 g, 86%). 1H NMR (400 MHz, CDCl3) δ 8.75-8.70 (2H, m), 8.23 (1H, d, J=8.5 Hz), 7.94 (1H, t, J=8.5 Hz), 7.80 (1H, t, J=8.5 Hz), 6.91 (1H, s), 5.79 (2H, s), 4.46 (2H, t, J=5.7 Hz), 3.99 (2H, t, J=5.2 Hz), 2.60 (3H, s), 0.67 (9H, s), −0.16 (6H, s). m/z (ES+) 507 (M+H+).

Provenance & Evidence