Reaktion #433877

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 56.4%

Lösungsmittel

acetonitrile

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux overnight under nitrogen
2. 2
   ExtraktionThe reaction mixture was extracted 3 times with dichloromethane
3. 3
   Waschenthe combined organic layers were washed with brine
4. 4
   Trocknendried over potassium carbonate
5. 5
   EinengenThe sample was concentrated on a rotary evaporator
6. 6
   Sonstigethe resulting oil was dried overnight under vacuum

Vorschrift

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).

Quelle