Reaction #1702130

Reaction equation

HCl

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

sodium hydroxide

→

desired product

Yield 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

Yield 65.0%

Solvents

tetrahydrofuran

water

Conditions

Workup

1. 1
   ExtractionThe aqueous layer was extracted with EtOAc twice
2. 2
   DryingThe combined organic layers were dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated (
5. 5
   Otherthen triturated with cold EtOAc)

Procedure

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).

Source