Trityl chloride → 2-Amino-9-(triphenylmethyl)-3,9-dihydro-6H-purin-6-one

Participants

Reaction Conditions

Reaction Steps

Guanine 5 (1.51 g, 9.99 mmol) and (NH4)2SO4 (100 mg) were suspended in HMDS (150 mL) and refluxed for 24 h. The solvent was evaporated under reduced pressure and the residue was dissolved in CH3CN (150 mL). Triphenylmethyl chloride (2.79 g, 10.0 mmol) was added and the reaction mixture was stirred at 25° C. for 7.0 h. The solution was concentrated under reduced pressure and the residue was purified by use of column chromatography (hexanes/EtOAc=1.5:8.5) to afford 6 (3.54 g, 8.99 mmol) in 90% yield: mp 268-270° C.; Rf(hexanes/EtOAc=1:2) 0.34; UV (EtOH) λmax 254 (ε 13,870), 278 (sh); 1H NMR (DMSO-d6) δ 5.97 (s, 2 H, NH2), 7.09-7.39 (m, 16 H, HC8+C(C6H5)3), 10.45 (br s, 1H, NH); MS m/z 393 (M+). Anal. (C24H19N5O) C, H, N; calcd (%): 73.26, 4.87, 17.80; found (%): 73.20, 4.81, 17.78.

Provenance & Evidence