تفاعل #799433

معادلة التفاعل

5-bromo-2-chloropyrimidine

water

ethyl 4-hydroxypiperidine-4-carboxylate

DIPEA

→

desired product

المردود 88.0%

Ethyl 1-(5-bromopyrimidin-2-yl)-4-hydroxypiperidine-4-carboxylate

المردود 88.0%

المذيبات

EtOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthen cooled to rt
2. 2
   استخلاصextracted with EtOAc (3×100 mL)
3. 3
   غسيلThe combined organics were washed with brine
4. 4
   تجفيفdried over anhydrous Na2SO4
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated under reduced pressure
7. 7
   أخرىThe crude residue was purified over 100-200 M silica-gel

الإجراء التجريبي

To an ice-cold solution of ethyl 4-hydroxypiperidine-4-carboxylate (0.60 g, 3.44 mmol) in EtOH (15 mL) was added DIPEA (2.95 mL, 17.24 mmol) followed by the addition of 5-bromo-2-chloropyrimidine (0.67 g, 3.44 mmol). The reaction was heated to 80° C. for 3 h then cooled to rt, water added and extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 20% EtOAc:hexane to obtain the desired product as a yellow solid (0.57 g, 88%). 1H NMR (DMSO-d6): δ 8.44 (s, 2H), 5.58 (s, 1H), 4.27 (m, 2H), 4.10 (q, J=7.20 Hz, 2H), 3.28 (m, 2H), 1.81 (m, 2H), 1.66 (m, 2H), and 1.18 (t, J=7.20 Hz, 3H).

المصدر