Reaction #40929

Reaction equation

Water

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

K2CO3

1-bromo-4-chloropentane

→

title compound

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

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 4 hours
2. 2
   Extractionthe resulting mixture was extracted with dichloromethane
3. 3
   Extractionextracted with DCM
4. 4
   OtherThe organic phases were dried
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crude product was purified by a silica SPE cartridge
7. 7
   Washeluting with DCM/MeOH from 98/2 to 95/5

Procedure

A mixture of 5-methyl-2,4(1H,3H)-pyrimidinedione (thimine, 500 mg) and K2CO3 (548 g) in dry DMF (15 mL) was stirred for 1 hour at room temperature. 1-bromo-4-chloropentane (0.548 mL) was then added and the mixture was stirred at room temperature for 4 hours. Water was then added and the resulting mixture was extracted with dichloromethane. The aqueous phase was acidified to pH 7 with aqueous 2% HCl solution and extracted with DCM. The organic phases were dried and concentrated in vacuo. The crude product was purified by a silica SPE cartridge eluting with DCM/MeOH from 98/2 to 95/5 to give the title compound (100 mg).

Source