Reaction #41016

Reaction equation

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

K2CO3

3-Bromo-1,1dimethoxy-propane

→

title compound

Yield 35.0%

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

Yield 35.0%

Solvents

DMF

Conditions

Workup

1. 1
   OtherSolvent was then removed under vacuum at 40° C.
2. 2
   Washthe residue washed with ethyl acetate
3. 3
   DryingThe organic phase was dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated
6. 6
   OtherThe crude was purified by flash chromatography
7. 7
   Washeluting with DCM-MeOH—NH4OH (98-2-0.2)

Procedure

A mixture of 5-(2-fluoro-6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 15, 667 mg, 2.59 mmol), and K2CO3 (358 mg, 2.59 mmol) in DMF (25 ml) was stirred 30 minutes at room temperature. Then 90% 3-Bromo-1,1dimethoxy-propane (432 μl, 2.85 mmol) was added in three portions during 3 days. Solvent was then removed under vacuum at 40° C. and the residue washed with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH—NH4OH (98-2-0.2) to give 291 mg of the title compound as a white solid (35% yield).

Source