تفاعل #76135

معادلة التفاعل

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

المردود 70.0%

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

المردود 70.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe THF was removed in vacuo
2. 2
   ترشيحcollected by filtration
3. 3
   أخرىdried in vacuo
4. 4
   أخرىit was reprecipitated from dichloromethane/hexanes

الإجراء التجريبي

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.

المصدر