Reaction #40975

Reaction equation

Ethyl acetate

K2CO3

5-(3-Fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione hydrochloride

3-Bromo-1,1dimethoxy-propane

→

title compound

Yield 22.0%

1-(3,3-Dimethoxy-propyl)-5-(3-fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione

Yield 22.0%

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGafter stirring
2. 2
   Otherthe reaction at room temperature for 48 hours
3. 3
   workup.WAITthe reaction was left at 4° C. for 17 days
4. 4
   Washthe mixture washed with water and brine
5. 5
   DryingThe organic phase was dried (Na2SO4)
6. 6
   Otherevaporated
7. 7
   OtherThe residue was purified by flash chromatography with DCM-MeOH—NH4OH 98-2-0.2

Procedure

5-(3-Fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 67, 243 mg, 1.1 mmol) was dissolved in DMF (2 ml). K2CO3 (153 mg, 1.1 mmol) was added and the mixture was stirred at room temperature for 1 hour. 3-Bromo-1,1dimethoxy-propane (225 mg, 1.11 mmol) was then added and after stirring the reaction at room temperature for 48 hours, the reaction was left at 4° C. for 17 days. Ethyl acetate was then added and the mixture washed with water and brine. The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography with DCM-MeOH—NH4OH 98-2-0.2 to afford 75 mg of the title compound (22% yield).

Source