Reaktion #88619

Reaktionsgleichung

1,6-dimethyl-5-nitropyrimidine-2,4(1H,3H)-dione

2-(3-bromopropoxy)tetrahydro-2H-pyran

K2CO3

→

1,6-dimethyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl) pyrimidine-2,4(1H,3H)-dione

Ausbeute 47.7%

Lösungsmittel

EA

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to RT
2. 2
   WaschenThe organic layer was washed with aq. 1N LiCl (3×30 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   Einengenconcentrated to a residue which
5. 5
   Sonstigewas purified by chromatography
6. 6
   Wascheneluted with PE/EA (5:1 to 1:1)

Vorschrift

To a solution of 1,6-dimethyl-5-nitropyrimidine-2,4(1H,3H)-dione (6 g, 0.032 mol) in DMF (20 mL) was added 2-(3-bromopropoxy)tetrahydro-2H-pyran (10.85 g, 0.049 mol) and K2CO3 (13.44 g, 0.097 mol). The reaction was heated at 65° C. for 2 h, cooled to RT then diluted with EA (20 mL) and water (20 mL). The organic layer was washed with aq. 1N LiCl (3×30 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (5:1 to 1:1) to give 1,6-dimethyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl) pyrimidine-2,4(1H,3H)-dione (5 g, 47.1% yield) as a yellow oil. LCMS: [MH+-THP] 244 and TR=1.180 min. Used without further purification.

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