Reaction #40926

Reaction equation

Water

5-methyl-2,4(1H,3H)-pyrimidinedione

K2CO3

1-bromo-4-chlorobutane

→

title compound

1-(4-chlorobutyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

Solvents

DMSO

Conditions

Workup

1. 1
   Extractionthe resulting mixture was extracted with EtAcO
2. 2
   Extractionextracted with DCM
3. 3
   WashThe organic phases were washed with brine
4. 4
   Dryingdried over Na2SO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crude product was purified by a silica SPE cartridge (25 g)
7. 7
   Washeluting with toluene/acetone from 95/5 to 75/25

Procedure

A mixture of 5-methyl-2,4(1H,3H)-pyrimidinedione (thimine, 500 mg, commercially available from Aldrich) and K2CO3 (546 mg) in dry DMSO (15 mL) was stirred for 1 hour at room temperature. 1-bromo-4-chlorobutane (0.46 mL) was then added and the mixture was stirred at room temperature for 20 hours. Water was then added and the resulting mixture was extracted with EtAcO. The aqueous phase was acidified to pH 7 with aqueous 2% HCl solution and extracted with DCM. The organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by a silica SPE cartridge (25 g) eluting with toluene/acetone from 95/5 to 75/25 to give the title compound as a colourless oil (250 mg).

Source