Reaktion #1283902

Reaktionsgleichung

1,3-dimethyl-6-[2-(2-hydroxyethylamino)ethylamino]-2,4-(1H,3H)-pyrimidinedione

1,3-dimethyl-6-[2-(2-hydroxyethylamino)ethylamino]-2,4(1H,3H)-pyrimidinedione

Compound 15

1,3-dimethyl-6-[2-(2-hydroxyethylamino)ethylamino]-2,4(1H,3H)-pyrimidinedione

3-(2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl bromide

Compound 16

3-(2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl bromide

oxalate

Compound 17

1,3-dimethyl-6-(2-[N-hydroxyethyl-N-[3-(2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl]amino]ethylamino)-2,4(1H,3H)-pyrimidinedione oxalate

→

1,3-dimethyl-6-(2-[N-hydroxyethyl-N-[3-(2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl]amino]ethyl-amino)-2,4(1H,3H)-pyrimidinedione

Ausbeute 55.0%

Lösungsmittel

N,N-dimethylformamide

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resultant reaction solution
2. 2
   Einengenwas concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in chloroform
4. 4
   Waschenwashed with water
5. 5
   WaschenThe thus water-washed chloroform layer
6. 6
   Trocknenwas dried over anhydrous sodium sulfate
7. 7
   Sonstigepurified through a silica gel column chromatograph (chloroform:methanol=98:2 to 96:4 in volume ratio) in odrer

Vorschrift

In 5 ml of N,N-dimethylformamide, reaction was carried out at 90° C. for 1 hour among 0.68 g of 1,3-dimethyl-6-[2-(2-hydroxyethylamino)ethylamino]-2,4-(1H,3H)-pyrimidinedione (Compound 15), 0.96 g of 3-(2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl bromide (Compound 16) and 1 ml of triethylamine. The resultant reaction solution was concentrated under reduced pressure, and the residue was dissolved in chloroform and then washed with water. The thus water-washed chloroform layer was dried over anhydrous sodium sulfate, and then purified through a silica gel column chromatograph (chloroform:methanol=98:2 to 96:4 in volume ratio) in odrer to obtain 0.75 g (yield 55%) of 1,3-dimethyl-6-(2-[N-hydroxyethyl-N-[3-(2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl]amino]ethyl-amino)-2,4(1H,3H)-pyrimidinedione (the non-oxalate of Compound 17).

Quelle