Sodium Azide → 2-[(S)-1-Phenylethylamino]-4-[5-azidobenzimidazol-1-yl]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A solution of 12 mg of NaNO2 in 0.5 mL of H2O was added to a 5° C. solution of 56 mg of 2-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine in 2 mL acetic acid. The solution was cooled to 0° C. and stirred for 0.5 hours. A solution of 16.5 mg NaN3 in 0.5 mL H2O was added and stirred for one hour. The solution was diluted with 100 mL of ethyl acetate and washed with water, saturated NaHCO3 and brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with methanol in methylene chloride to give 53 mg of the title compound. RF: 0.6 (5% MeOH in CH2Cl2). 1H NMR (400 MHz, 1:1 CD3OD/CDCl3): δ 1.60 (d, J=7.0 Hz, 3H), 5.12 (q, J=7.0 Hz, 1H), 6.8 (m, 1H), 6.95 (d, J=6 Hz, 1H), 7.2-7.45 (m, 6H), 7.72 (m, 1H), 8.33 (br s, J=6.5 Hz, 1H), 8.74 (m, 1H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 357.1 (M+1).

Provenance & Evidence