Sodium borohydride → [5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-2-yl}methanol

Participants

Reaction Steps

To a solution of methyl 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylate (prepared in an analogous manner to Example 279, 500 mg, 1.23 mmol) in anhydrous THF (50 mL) at 0 C, was added sodium borohydride (95 mg, 2.46 mmol) portion-wise under nitrogen. The resulting solution was sonicated briefly and stirred at 40 C for 1 h. The reaction mixture was then allowed to stir at room temperature for a further 16 h. The reaction was quenched with water (25 mL) and extracted with EtOAc (3×25 mL). Combined organics were dried over magnesium sulfate and evaporated to dryness to afford the crude product as a yellow solid. The solid was triturated with MeOH, filtered and washed further with diethyl ether (100 mL) to afford the title compound as a salmon coloured solid (305 mg, 67%).

Provenance & Evidence