Reaction #41019

Reaction equation

3-Bromo-1, 1dimethoxy-propane

5-pyridazin-3-yl-1H-pyrimidine-2,4-dione hydrochloride

3-bromo-1,1dimethoxy-propane

K2CO3

3-Bromo-1,1dimethoxy-propane

→

title compound

Yield 24.0%

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

Yield 24.0%

Solvents

DMSO

Conditions

Workup

1. 1
   workup.WAITthe reaction was left for 11 days at room temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITcontinued for additional 6 days
4. 4
   Washthe residue washed with diethyl ether and filtrate
5. 5
   WashThe solid washed with ethyl acetate
6. 6
   OtherAfter evaporation of the organic phase

Procedure

A mixture of 5-pyridazin-3-yl-1H-pyrimidine-2,4-dione hydrochloride (Prep121, 656 mg, 2.89 mmol), 3-bromo-1,1dimethoxy-propane (609 mg, 3.33 mmol) and K2CO3 (400 mg, 2.89 mmol) in DMSO (10 ml) was stirred for 24 hours at room temperature. 3-Bromo-1, 1dimethoxy-propane (100 mg, 0.55 mmol) was then added and the reaction was left for 11 days at room temperature. 3-Bromo-1,1dimethoxy-propane (100 mg, 0.55 mmol) was further added and stirring continued for additional 6 days. The mixture was lyophilized and the residue washed with diethyl ether and filtrate. The solid washed with ethyl acetate. After evaporation of the organic phase, 200 mg of the title compound as a light brown powder was obtained (24% yield).

Source