Reacción #76135

Ecuación de reacción

tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

NaOH

water

→

title compound

Rendimiento 70.0%

tert-Butyl 4-[N-[7-Chloro-2-hydroxymethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Rendimiento 70.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe THF was removed in vacuo
2. 2
   Filtracióncollected by filtration
3. 3
   Otrodried in vacuo
4. 4
   Otroit was reprecipitated from dichloromethane/hexanes

Procedimiento

To a solution of tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (0.070 g, 0.14 mmol) in THF (2.7 ml) was dropwise added aqueous NaOH (1N, 0.27 ml, 0.27 mmol) followed by water (0.2 ml). The reaction mixture was stirred at room temperature for 2 hours, then the THF was removed in vacuo. The residue was suspended in water (10 ml) and the pH was adjusted to ˜5 with 1N HCl. The white precipitate was. collected by filtration, dried in vacuo and then it was reprecipitated from dichloromethane/hexanes to afford the title compound as a white solid (0.044 g, 70%), mp 185-187° C.; 1H-NMR (DMSO-d6) 1.49 (s, 9H, But), 3.25 (s, 1H, C≡CH), 4.35, 4.38 (2×s, 4H, CH2C≡C and 2-CH2), 4.78 (s, 2H, 6-CH2), 5.62 (br s, 1H, OH), 6.78 (d, J=8.7 Hz, 2H, 3′,5′-ArH), 7.73 (d, J=8.6 Hz, 2H, 2′,6′-ArH), 7.78, 7.84 (2×s, 2H, 5-H, 8-H), 12.07 (s, 1H, N3—H); FAB-HRMS: measured: 453.1463, calculated for C24H24ClN3O4: 453.1455.

Fuente