1-bromo-4-chloropentane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). the mixture was stirred at room temperature for 4 hours the resulting mixture was extracted with dichloromethane extracted with DCM The organic phases were dried concentrated in vacuo The crude product was purified by a silica SPE cartridge eluting with DCM/MeOH from 98/2 to 95/5

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). the mixture was stirred at room temperature for 4 hours the resulting mixture was extracted with dichloromethane extracted with DCM The organic phases were dried concentrated in vacuo The crude product was purified by a silica SPE cartridge eluting with DCM/MeOH from 98/2 to 95/5

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). the mixture was stirred at room temperature for 4 hours the resulting mixture was extracted with dichloromethane extracted with DCM The organic phases were dried concentrated in vacuo The crude product was purified by a silica SPE cartridge eluting with DCM/MeOH from 98/2 to 95/5