反应详情

温度

75 °C

To a solution of 2-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine (EXAMPLE 79) (80 mg) in acetic acid (2 mL) was added triethyl orthoformate (123 μL). The reaction was stirred at room temperature for 1 h, at 75° C. for 2 h, and then at room temperature again overnight (≈14 h). NaN3 (47 mg, 3 eq.) was added; the reaction was stirred at 75° C. for 5 h. The reaction was cooled, quenched with water, extracted with methylene chloride. The organic solution was washed with water and brine; it was dried over Na2SO4. Removal of the solvent and subsequent purification by preparative thin layer chromatography (acetone:hexane=1:1) provided the title compound (20 mg). Mass spectrum (ESI): 384 (M+1). 1H NMR (500 MHz, CDCl3): δ 9.04 (s, 1H); 8.56 (br s, 1H); 8.46 (d, J=5.2 Hz, 1H); 8.08 (s, 1H); 7.82 (br s, 1H); 7.57 (br s, 1H); 7.50-7.25 (m, 5H); 6.79 (d, J=5.3 Hz, 1H); 5.88 (br s, 1H); 5.18 (br s, 1H); 1.67 (d, J=6.8 Hz, 3H).

1. customat room temperature
2. customagain overnight (≈14 h)
3. stirringthe reaction was stirred at 75° C. for 5 h
4. temperatureThe reaction was cooled
5. customquenched with water
6. extractionextracted with methylene chloride
7. washThe organic solution was washed with water and brine
8. dry with materialit was dried over Na2SO4
9. customRemoval of the solvent and subsequent purification by preparative thin layer chromatography (acetone:hexane=1:1)