Reaction #41009

Reaction equation

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

Yield 42.0%

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

Yield 42.0%

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction mixture stirred for additional 2 days
2. 2
   Washthe aqueous layer washed with diethylether
3. 3
   Extractionthe product extracted with ethyl acetate
4. 4
   DryingThe organic phase was dried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe crude was purified by flash chromatography
8. 8
   Washeluting with ethyl acetate-NH4OH (100-0.25)

Procedure

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).

Source