Reaktion #41009

Reaktionsgleichung

3-Bromo-1,1dimethoxy-propane

5-(2-Chloro-6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride

K2CO3

3-bromo-1,1dimethoxy-propane

Water

→

title compound

Ausbeute 42.0%

5-(2-Chloro-6-methyl-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione

Ausbeute 42.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture stirred for additional 2 days
2. 2
   Waschenthe aqueous layer washed with diethylether
3. 3
   Extraktionthe product extracted with ethyl acetate
4. 4
   TrocknenThe organic phase was dried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe crude was purified by flash chromatography
8. 8
   Wascheneluting with ethyl acetate-NH4OH (100-0.25)

Vorschrift

A mixture of 5-(2-Chloro-6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep107, 345 mg, 1.27 mmol), K2CO3 (174 mg, 1.27 mmol) and 3-bromo-1,1dimethoxy-propane (86 μl, 0.63 mmol) in DMF (3 ml) was stirred at room temperature overnight. 3-Bromo-1,1dimethoxy-propane (86 μl, 0.63 mmol) was then added and the reaction mixture stirred for additional 2 days. Water was added and the aqueous layer washed with diethylether and then the product extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography eluting with ethyl acetate-NH4OH (100-0.25) to give 90 mg of the title compound (21% yield).

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