Reaktion #50213

Reaktionsgleichung

5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

imidazole

potassium carbonate

iodine

→

title compound

Ausbeute 38.0%

5-[2-Ethoxy-5-(1-imidazolyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Ausbeute 38.0%

Lösungsmittel

water

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux under nitrogen for 4.5 hours
2. 2
   Temperaturcooled
3. 3
   ExtraktionThis mixture was extracted with a 9:1 mixture of dichloromethane and methanol (6×50 ml)
4. 4
   Trocknendried (MgSO4)
5. 5
   Sonstigeevaporated under vacuum
6. 6
   Sonstigeto give a pale brown oil
7. 7
   SonstigeThe oil was chromatographed on silica gel (20 g)
8. 8
   Wascheneluting with a mixture of dichloromethane, methanol and triethylamine (97.8:20:0.2)
9. 9
   Sonstigeto give
10. 10
    Sonstigea yellow solid, crystallisation of which from ethyl acetate-hexane

Vorschrift

A solution of 5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (0.20 g, 0.0051 mol), imidazole (0.172 g, 0.0025 mol), anhydrous potassium carbonate (0.077 g, 0.00056 mol), copper bronze (0.036 g, 0.00057 mol) and iodine (0.015 g, 0.00012 mol) in dimethylformamide (10 ml) was heated under reflux under nitrogen for 4.5 hours, cooled and poured into water (50 ml). This mixture was extracted with a 9:1 mixture of dichloromethane and methanol (6×50 ml) and the extracts combined, dried (MgSO4) and evaporated under vacuum to give a pale brown oil. The oil was chromatographed on silica gel (20 g), eluting with a mixture of dichloromethane, methanol and triethylamine (97.8:20:0.2), to give a yellow solid, crystallisation of which from ethyl acetate-hexane gave the title compound as a cream solid (0.073 g, 38%), m.p. 193°-194° C. Found: C,63.61; H,5.97; N,22.03. C20H22N6O2 requires C,63.48; H,5.86; N,22.21%.

Quelle