4-Aminophenol → HCID 67242656, compound

Participants

Reaction Steps

A mixture of 10 mmol (2387 mg) 6-chloro-9-(tetrahydropyran-2-yl)purine (prepared from 10 mmol (1546 mg) of 6-chloropurine), 12 mmol (1309 mg) of 4-hydroxyphenylamine (4-hydroxyaniline) and 4 ml of N-ethyldiisopropylamine was refluxed in n-butanol for 3 hrs. After removal of the n-butanol by vacuum evaporation, the resulting material was treated with water and extracted into ethyl acetate. The ethyl acetate solvent was evaporated and the residuum subsequently washed with 30 ml of ether. The solid residue was filtered off and the crude product crystallized from methanol. Yield: 90%, white solid. TLC (CHCl3:CH3OH:NH3) (90:10:0.1) (v:v): single spot; HPLC: purity >98%. 1H NMR (400 MHz, DMSO): 1.56tt (2H, Ja=11.0 Hz, Jb=3.3 Hz); 1.72qq (1H, Ja=11.6 Hz, Jb=3.3 Hz); 1.94tt (2H, Ja=11.0 Hz, Jb=3.3 Hz); 2.28qq (1H, Ja=11.6 Hz, Jb=3.3 Hz); 3.66m (1H); 3.98dd (1H, Ja=11.0 Hz, Jb=2.1 Hz); 5.62dd (1H, Ja=11.0 Hz, Jb=2.1 Hz); 7.02d (2H, J=8.5 Hz); 8.19s (1H); 8.26d (2H, J=8.5 Hz); 8.29s (1H); 8.95s (1H). MS (ES+): [M+H]+=312 (100).

Provenance & Evidence