Reacción #1702130

Ecuación de reacción

HCl

3-{2-[(2-{[3-(bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol

sodium hydroxide

→

desired product

Rendimiento 65.0%

19-Chloro-9-oxa-2,17,21,22-tetraazatetracyclo[16.3.1.1(3,7).1(10,14)]tetracosa-1(22),3(24),4,6,10(23),11,13,18,20-nonaene

Rendimiento 65.0%

Disolventes

tetrahydrofuran

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe aqueous layer was extracted with EtOAc twice
2. 2
   SecadoThe combined organic layers were dried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated (
5. 5
   Otrothen triturated with cold EtOAc)

Procedimiento

To a solution of 3-{2-[(2-{[3-(bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol (25.0 mg, 0.0576 mmol) in tetrahydrofuran (0.561 mL) was added a solution of sodium hydroxide in water (0.46 mL, 0.50 M). The resultant solution was stirred at rt for 16 hours until the reaction was complete. The reaction mixture was neutralized with aqueous HCl solution (3 M) to pH 7. The aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated (then triturated with cold EtOAc) to give the desired product as an off-white powder (13 mg, 65%). LCMS for C19H18ClN4O (M+H)+: m/z=353.0. 1H NMR (400 MHz, CD3OD): δ 7.72 (s, 1H), 7.52 (s, 1H), 7.29 (t, J=7.6 Hz, 1H), 7.19 (s, 1H), 7.10 (dd, J=7.6, 0.8 Hz, 1H), 7.06 (t, J=7.2 Hz, 1H), 6.93 (dd, J=7.2, 0.8 Hz, 1H), 6.73 (dd, J=2.4, 0.8 Hz, 1H), 6.66 (d, J=7.2 Hz, 1H), 5.25 (s, 2H), 3.70 (m, 2H), 2.72 (t, J=6.8 Hz, 1H).

Fuente