Reaction #41002

Reaction equation

Water

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

K2CO3

3-Bromo-1,1dimethoxy-propane

→

final compound

Yield 53.3%

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

Yield 53.3%

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for three days
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 (95:5:0.5)

Procedure

A mixture of 5-(2-fluoro-5-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep99, 300 mg, 1.16 mmol), and K2CO3 (241 mg, 1.7 mmol) in DMF (5 ml) was stirred for one hour at room temperature. 3-Bromo-1,1dimethoxy-propane (234 mg, 1.3 mmol) was added and stirring was continued for three days. Water was added and 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 (95:5:0.5) to give 200 mg of the final compound as oil (53% yield).

Source