تفاعل #433877

معادلة التفاعل

DIEA

N-methyl-4(methylamino)piperidine

152

N-Azepan-yl-6-chloro-N′-(3-chloro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine

→

ammonium hydroxide

solid 154

المردود 56.4%

N-Azepan-1-yl-N′-(3-chloro-4-methoxy-phenyl)-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine

المردود 56.4%

المذيبات

acetonitrile

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux overnight under nitrogen
2. 2
   استخلاصThe reaction mixture was extracted 3 times with dichloromethane
3. 3
   غسيلthe combined organic layers were washed with brine
4. 4
   تجفيفdried over potassium carbonate
5. 5
   تركيزThe sample was concentrated on a rotary evaporator
6. 6
   أخرىthe resulting oil was dried overnight under vacuum

الإجراء التجريبي

To 152 (0.2007 g, 0.5 mmol) dissolved in THF (10 mL) was added a solution of N-methyl-4(methylamino)piperidine (0.07 mL, 0.5 mmol) in THF (1 mL) followed by the addition of DIEA (1.0 mL, 0.55 mmol) in acetonitrile (1 mL). The reaction mixture was allowed to stir at reflux overnight under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (90:9:1 dichloromethane: methanol: conc. ammonium hydroxide) yielded a light yellow solid 154 (65 mg, 27%), mp 100° C.; TLC (silica gel, 90:9:1 CH2Cl2: CH3OH, conc. NH4OH), Rf 0.36; MS (ESI): m/z 475 (M+H, 23.2), 378 (11.6), 258 (68.9), 239 (52.2), 238 (100).

المصدر