Nitrogen → 1-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-ylamine

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(4-nitro-pyrazol-1-ylmethyl)-oxazole (408 mg, 1.20 mmol), iron powder (204 mg, 3.62 mmol) and NH4Cl (326 mg, 6.03 mmol) in a mixture of EtOH (6.0 mL) and water (3.0 mL) was stirred at 75° C. for 45 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. The residue was redissolved in CH2Cl2 (20 mL), dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil. TLC: rf (EA)=0.20. LC-MS-conditions 02: tR=0.81 min; [M+H]+=309.07.

Provenance & Evidence