تفاعل #4543

معادلة التفاعل

4

2-Amino-6-chloro-4-methyl-3,5-pyridinedicarbonitrile

MeOH

cyclohexane EtOAc

→

2-Amino-4-methyl-3,5-pyridinedicarbonitrile

المردود 86.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىfor six hours
2. 2
   ترشيحThe mixture was then filtered (Celite mat)
3. 3
   أخرىevaporated to dryness (final conditions <1 mm, bath to 45° C.) The residue
4. 4
   workup.ADDITIONcontaining Ba salts which
5. 5
   أخرىseparated during the evaporation
6. 6
   أخرىto give the H2O-insoluble product (7.74 g)
7. 7
   أخرىRecrystallization from EtOH (800 mL)
8. 8
   أخرىthen gave pure 6, mp 222°-223° C.

الإجراء التجريبي

Hydrogenolysis of 4 (10.0 g, 52.0 mmol) in DMF (150 mL)-MeOH (75 mL) containing 5% Pd on BaCO3 (10.0 g) was carried out in a Parr shaker with H2 pressure kept near 3.5 kg/cm2 (50 psi) for six hours. The mixture was then filtered (Celite mat), and evaporated to dryness (final conditions <1 mm, bath to 45° C.) The residue containing Ba salts which separated during the evaporation was stirred with H2O (100 mL) to give the H2O-insoluble product (7.74 g). Recrystallization from EtOH (800 mL) then gave pure 6, mp 222°-223° C., in 86% yield (7.1 g); homogeneous by TLC (cyclohexane-EtOAc, 1:1); 1H NMR (Me2SO-d6) δ2.50 (s, CH3), 7.82 (s, NH2), 8.50 (s, C2 --H).

المصدر