Reaction #41023

Reaction equation

Water

5-pyrazin-2-yl-1H-pyrimidine-2,4-dione hydrochloride

5-Pyrazin-2-yl-1H-pyrimidine-2,4-dione hydrochloride

K2CO3

3-Bromo-1,1dimethoxy-propane

→

title compound

Yield 35.0%

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

Yield 35.0%

Solvents

DMF

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   DryingThe organic phase was dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated
5. 5
   OtherThe crude was purified by flash chromatography
6. 6
   Washeluting with DCM-MeOH—NH4OH (98-2-0.2)

Procedure

A mixture of 5-pyrazin-2-yl-1H-pyrimidine-2,4-dione hydrochloride (Prep125, 2.19 mmol), and K2CO3 (302 mg, 2.19 mmol) in DMF (20 ml) was stirred 30 minutes at room temperature. 90% 3-Bromo-1,1dimethoxy-propane (365 μl, 2.41 mmol) was added in two portions during 2 days. Water was added and the mixture 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 (98-2-0.2) to give 221 mg of the title compound (35% yield).

Source