تفاعل #1702137

معادلة التفاعل

HCl

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

sodium hydroxide

→

desired product

المردود 20.0%

20-Chloro-9-oxa-2,18,22,23-tetraazatetracyclo[17.3.1.1(3,7).1(10,14)]pentacosa-1(23),3(25),4,6,10(24),11,13,19,21-nonaene

المردود 20.0%

المذيبات

tetrahydrofuran

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe aqueous layer was extracted with EtOAc twice
2. 2
   تجفيفThe combined organic layers were dried over Na2SO4
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىto give the crude product, which
6. 6
   أخرىwas purified by silica gel column chromatography

الإجراء التجريبي

To a solution of 3-{3-[(2-{[3-(bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]propyl}phenol (50.0 mg, 0.112 mmol) in tetrahydrofuran (1.09 mL) was added a solution of sodium hydroxide in water (0.893 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 HCl (3 M aqueous solution) to pH=7. The aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the crude product, which was purified by silica gel column chromatography to give the desired product as a white powder (8 mg, 20%). LCMS for C20H20ClN4O (M+H)+: m/z=367.0. 1H NMR (400 MHz, CD3OD): δ 7.94 (s, 1H), 7.75 (s, 1H), 7.26 (m, 1H), 7.17 (m, 2H), 7.03 (t, J=7.6 Hz, 1H), 6.88 (m, 1H), 6.70 (m, 1H), 6.60 (m, 1H), 5.17 (s, 2H), 3.48 (t, J=7.6 Hz, 2H), 2.74 (t, J=6.8 Hz, 2H), 1.91 (m, 2H).

المصدر