Réaction #76135

Équation de réaction

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

Rendement 70.0%

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

Rendement 70.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autrethe THF was removed in vacuo
2. 2
   Filtrationcollected by filtration
3. 3
   Autredried in vacuo
4. 4
   Autreit was reprecipitated from dichloromethane/hexanes

Mode opératoire

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.

Source