反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
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).
WORKUP
后处理
- stirringstirred for one hour
- washwashed with water, saturated NaHCO3 and brine
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography
- washeluting with methanol in methylene chloride