Sodium Azide → 2-[(S)-1-Phenylethylamino]-4-[6-azidobenzimidazol-1-yl]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A solution of 16.3 mg of NaNO2 in 0.5 mL of H2O was added to a 5° C. solution of 78 mg of 2-[(S)-1-phenylethylamino]-4-[6-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 23 mg of 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 62 mg of the title compound. RF: 0.6 (5% MeOH in CH2Cl2). 1H NMR (300 MHz, CD3OD): δ1.57 (d, J=7 Hz, 3H), 5.18 (q, J=8 Hz, 1H), 6.88 (d, J=6 Hz, 1H), 7.05 (dd, J=2.5, 9 Hz, 1H), 7.18 (m, 1H), 7.29 (t, J=6 Hz, 2H), 7.43 (d, J=9 Hz, 2H), 7.65 (d, J=9 Hz, 1H), 8.02 (m, 1H), 8.3 (d, J=6 Hz, 1H), 8.69 (b s, 1H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 357.2 (M+1).

Provenance & Evidence