Reaktion #76850

Reaktionsgleichung

1-(4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-hydrochloride

triethylamine

bromo-pyrimidin-acetic acid ethyl ester

→

title product

Ausbeute 63.1%

1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-pyrimidin-acetic acid ethyl ester

Ausbeute 63.1%

Lösungsmittel

DMF

AcOEt

AcOEt

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux under argon for 20 h
2. 2
   TemperaturAfter cooling
3. 3
   Waschenwashed with water
4. 4
   ExtraktionThe aqueous phase was extracted twice with CH2Cl2
5. 5
   Trocknenthe combined organic phases were dried over anhydrous AcOEt
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto give a crude brown-orange oil

Vorschrift

To a white suspension of 1-(4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-hydrochloride (1.65 g, 4.36 mmol) in dry DMF (5 ml), were added triethylamine (1.82 ml, 0.013 mol) and bromo-pyrimidin-acetic acid ethyl ester (1.07 g, 4.36 mmol). The reaction mixture was stirred at reflux under argon for 20 h. After cooling, the mixture was diluted in AcOEt and washed with water. The aqueous phase was extracted twice with CH2Cl2, the combined organic phases were dried over anhydrous AcOEt, filtered and concentrated to give a crude brown-orange oil. Flash chromatography (AcOEt) gave 1.4 g (63%) of the title product as a brown-orange oil.

Quelle