Reaction #40994

Reaction equation

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

K2CO3

3-Bromo-1,1dimethoxy-propane

→

title compound

Yield 40.0%

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

Yield 40.0%

Solvents

DMF

Conditions

Workup

1. 1
   OtherSolvent was then removed under vacuum at 40° C.
2. 2
   Washthe residue washed once with petroleum ether and twice with ethyl acetate
3. 3
   DryingEthyl acetate 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-(6-chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep91, 1.05 g, 4.10 mmol), and K2CO3 (565 mg, 4.10 mmol) in DMF (20 ml) was stirred 20 minutes at room temperature. 3-Bromo-1,1dimethoxy-propane (635 μl, 4.65 mmol) was added in three portions over 6 days. Solvent was then removed under vacuum at 40° C. and the residue washed once with petroleum ether and twice with ethyl acetate. Ethyl acetate 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 534 mg of the title compound as a white solid (40% yield).

Source