Reaction #41012

Reaction equation

Water

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

K2CO3

3-bromo-1,1dimethoxy-propane

→

title compound

Yield 27.0%

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

Yield 27.0%

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONwas added in two portions over 2 days
2. 2
   Washwashed with Et2O
3. 3
   Extractionthe product was 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 DCM-MeOH—NH4OH (98-2-02)

Procedure

To a mixture of 5-(4-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 11, 605 mg, 2.53 mmol) and K2CO3 (349 mg, 2.53 mmol) in DMF (10 ml), 3-bromo-1,1dimethoxy-propane (399 μl, 2.78 mmol) was added in two portions over 2 days and the mixture was contemporarily stirred at room temperature. Water was then added and washed with Et2O, the product was extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH—NH4OH (98-2-02) to give 100 mg of the title compound (27% yield).

Source