Reaction #40998

Reaction equation

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

K2CO3

3-bromo-1,1dimethoxy-propane

→

final compound

Yield 40.0%

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

Yield 40.0%

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONwas added in three portions over 5 days
2. 2
   OtherSolvent was then removed in vacuum at 40° C
3. 3
   WashThe residue washed with petroleum ether
4. 4
   DryingEthyl acetate 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 (98:2:0.2)

Procedure

To a suspension of 5-(2-chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride salt (Prep95, 803 mg, 3.10 mmol) and K2CO3 (428 mg, 3.10 mmol) in DMF (15 ml), 90% 3-bromo-1,1dimethoxy-propane (516 μl, 3.41 mmol) was added in three portions over 5 days. The mixture was contemporarily stirred at room temperature. Solvent was then removed in vacuum at 40° C. The residue washed with petroleum ether and then 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 400 mg of the final compound as a white solid (40% yield)

Source